dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-806e866817ed4153a7c9759228662d83 | CC1CN1.Cc1cc(C)c(Cc2ccc(C(C)C)cc2)c(OCC(=O)O)c1>>Cc1cc(C)c(Cc2ccc(C(C)C)cc2)c(OCC(=O)N2CC2C)c1 | C(C)(C)C1=CC=C(CC2=C(OCC(=O)O)C=C(C=C2C)C)C=C1.C(C(=O)Cl)(=O)Cl.CC1CN1.C(C)N(CC)CC>>C(C)(C)C1=CC=C(CC2=C(OCC(=O)N3C(C3)C)C=C(C=C2C)C)C=C1 | [NH:22]1[CH2:23][CH:24]1[CH3:25].O[C:20]([CH2:19][O:18][c:17]1[c:6]([CH2:7][c:8]2[cH:9][cH:10][c:11]([CH:12]([CH3:13])[CH3:14])[cH:15][cH:16]2)[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:26]1)=[O:21]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([CH2:7][c:8]2[cH:9][cH:10][c:11]([CH:12]([CH3:13])[CH3:14])[cH:15][cH:16]2)[c:17]([O:1... | CC1CN1.Cc1cc(C)c(Cc2ccc(C(C)C)cc2)c(OCC(=O)O)c1 | Cc1cc(C)c(Cc2ccc(C(C)C)cc2)c(OCC(=O)N2CC2C)c1 | null | CN(C)C=O | O.C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | 9ca982ea297a848b235cc8eed70749cbb740c3a9eeb5e2bbe24b3ac10d9db7ba | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(COc1ccccc1Cc1ccccc1)N1CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[C;D1;H3:5]-[C:6]1-[C:7]-[NH;D2;+0:8]-1>>[#8:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:8]1-[C:7]-[C:6]-1-[C;D1;H3:5] | 99 | [{"value": 99.0, "product": "C(C)(C)C1=CC=C(CC2=C(OCC(=O)N3C(C3)C)C=C(C=C2C)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of (2-(4-isopropylbenzyl)-3,5-dimethylphenoxy)acetic acid obtained in Reference Example 157 (9.00 g, 28.8 mmol) in THF (90 mL) was added dropwise oxalylchloride (3.77 mL, 43.2 mmol) with ice-cooling, and was then added DMF (four drops), and then the mixture was stirred for 30 minutes. The reaction solutio... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CN1 | C1C[NH]1 | c1ccccc1.c1ccccc1.C1C[NH]1 | HO- | CN(C)C=O.O.C1CCOC1 | null | 0.5 | CC1CN1.Cc1cc(C)c(Cc2ccc(C(C)C)cc2)c(OCC(=O)O)c1>CN(C)C=O.O.C1CCOC1>Cc1cc(C)c(Cc2ccc(C(C)C)cc2)c(OCC(=O)N2CC2C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-163546329c8d4d4eb6023eb903dae6b2 | CC(=O)Oc1cc(C)c(OC(C)=O)c2ccccc12>>CC(=O)Oc1c(C)cc(O)c2ccccc12 | Cl.O.C(C)(=O)OC1=C(C=C(C2=CC=CC=C12)OC(C)=O)C.C([O-])([O-])=O.[K+].[K+]>>C(C)(=O)OC1=C(C=C(C2=CC=CC=C12)O)C | CC(=O)[O:10][c:9]1[cH:8][c:6]([CH3:7])[c:5]([O:4][C:2]([CH3:1])=[O:3])[c:16]2[c:11]1[cH:12][cH:13][cH:14][cH:15]2>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[c:6]([CH3:7])[cH:8][c:9]([OH:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]12 | CC(=O)Oc1cc(C)c(OC(C)=O)c2ccccc12 | CC(=O)Oc1c(C)cc(O)c2ccccc12 | null | null | CO | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | db7d50f1ad65e3456617ab9bc6ab5b9ede0e069a6dd971d117a653e2a40b05de | efe1c37482b229370967d04d1a68db10ee663983a92b84fa0f009f5bb178597f | c1ccc2ccccc2c1 | C-C(=O)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 100.3 | [{"value": 100.3, "product": "C(C)(=O)OC1=C(C=C(C2=CC=CC=C12)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a solution of 4-(acetyloxy)-2-methyl-1-naphthyl acetate (25 g, 96.8 mmol) in methanol (300 mL) was added potassium carbonate (58.1 g, 420 mmol), and the mixture was stirred under argon atmosphere at room temperature for 15 minutes. Water was poured into the mixture, which was neutralized with hydrochloric acid and t... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aromatic alcohol | null | null | c1ccc2ccccc2c1 | HO- | CO | null | 0.25 | CC(=O)Oc1cc(C)c(OC(C)=O)c2ccccc12>CO>CC(=O)Oc1c(C)cc(O)c2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-79f04663d6d947b1861e50fbfaee70bc | CCOC(=O)/C=C(\C)CP(=O)(OCC)OCC.O=C1CCCCC1>>CCOC(=O)C=C(C)C=C1CCCCC1 | CCOC(=O)/C=C(\C)/CP(=O)(OCC)OCC.O.[H-].[Na+].C1(CCCCC1)=O>>C1(CCCCC1)=CC(=CC(=O)OCC)C | CCOP(=O)(OCC)[CH2:9]/[C:7](=[CH:6]/[C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:8].O=[C:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[C:7]([CH3:8])[CH:9]=[C:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1 | CCOC(=O)/C=C(\C)CP(=O)(OCC)OCC.O=C1CCCCC1 | CCOC(=O)C=C(C)C=C1CCCCC1 | null | null | CN(C)C=O | C-C Coupling | Wittig with Phosphonium | 4ce37e7cfa5efcdc26b09d9194baaf9836bdf303013ec691bac1ea4e9c083013 | 06a42e352cf517302d592bf38a2fd11b220014e39071074dc7becb6ee0bee4b2 | [CH]=C1CCCCC1 | C-C-O-P(=O)(-O-C-C)-[CH2;D2;+0:1]/[C:2](-[C;D1;H3:3])=[C:4]/[C:5](-[#8:6])=[O;D1;H0:7].O=[C;H0;D3;+0:8](-[C:9]-[C:10])-[C:11]-[C:12]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]=[C:2](-[C;D1;H3:3])-[CH;D2;+0:1]=[C;H0;D3;+0:8](-[C:9]-[C:10])-[C:11]-[C:12] | null | [] | null | null | 1 | HOUR | To a suspension of sodium hydride (a 60% liquid paraffin dispersion, 1.8 g, 40 mmol) in DMF (60 mL) was added triethyl 3-methyl-4-phosphonocrotonate (11 g, 41.6 mmol) at 0° C., and the mixture was stirred at room temperature for 1 hour. To the reaction solution was added cyclohexanone (3.93 g, 40 mmol), and the mixture... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | C1CCCCC1 | C1CCCCC1 | C1CCCCC1 | HO- | CN(C)C=O | null | 1 | CCOC(=O)/C=C(\C)CP(=O)(OCC)OCC.O=C1CCCCC1>CN(C)C=O>CCOC(=O)C=C(C)C=C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f563f646f2b34ddcb36c6be94de3e454 | CC(=O)Oc1cc(C)cc2c1CCCC2>>Cc1cc(O)c2c(c1)CCCC2 | C(C)(=O)OC1=CC(=CC=2CCCCC12)C.[OH-].[Na+]>>CC=1C=C(C=2CCCCC2C1)O | CC(=O)[O:5][c:4]1[cH:3][c:2]([CH3:1])[cH:8][c:7]2[c:6]1[CH2:12][CH2:11][CH2:10][CH2:9]2>>[CH3:1][c:2]1[cH:3][c:4]([OH:5])[c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][CH2:11][CH2:12]2 | CC(=O)Oc1cc(C)cc2c1CCCC2 | Cc1cc(O)c2c(c1)CCCC2 | null | null | CO.C1CCOC1 | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | db7d50f1ad65e3456617ab9bc6ab5b9ede0e069a6dd971d117a653e2a40b05de | efe1c37482b229370967d04d1a68db10ee663983a92b84fa0f009f5bb178597f | c1ccc2c(c1)CCCC2 | C-C(=O)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 99 | [{"value": 99.0, "product": "CC=1C=C(C=2CCCCC2C1)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a mixed solution of 3-methyl-5,6,7,8-tetrahydro-1-naphthalenyl acetate synthesized in Reference Example 173 (5.1 g, 25.1 mmol) in THF (120 mL) and methanol (30 mL) was added 12 N aqueous sodium hydroxide solution (2.5 mL) at room temperature, and the mixture was stirred for 30 minutes, and then concentrated under re... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aromatic alcohol | null | null | c1ccc2c(c1)CCCC2 | HO- | CO.C1CCOC1 | null | 0.5 | CC(=O)Oc1cc(C)cc2c1CCCC2>CO.C1CCOC1>Cc1cc(O)c2c(c1)CCCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-38527b9b346c41dcbacd909ffc5940c2 | CC(=O)Oc1cc(C)cc2c1CCC2>>Cc1cc(O)c2c(c1)CCC2 | C(C)(=O)OC1=C2CCCC2=CC(=C1)C>>CC=1C=C(C=2CCCC2C1)O | CC(=O)[O:5][c:4]1[cH:3][c:2]([CH3:1])[cH:8][c:7]2[c:6]1[CH2:11][CH2:10][CH2:9]2>>[CH3:1][c:2]1[cH:3][c:4]([OH:5])[c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][CH2:11]2 | CC(=O)Oc1cc(C)cc2c1CCC2 | Cc1cc(O)c2c(c1)CCC2 | null | null | CCCCCC.C(C)(=O)OCC | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | db7d50f1ad65e3456617ab9bc6ab5b9ede0e069a6dd971d117a653e2a40b05de | efe1c37482b229370967d04d1a68db10ee663983a92b84fa0f009f5bb178597f | c1ccc2c(c1)CCC2 | C-C(=O)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 81 | [{"value": 81.0, "product": "CC=1C=C(C=2CCCC2C1)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 6-methyl-2,3-dihydro-1H-inden-4-yl acetate synthesized in Reference Example 174, the title compound was synthesized in the same manner as in Reference Example 175. Yield 81%. Melting point: 82-83° C. (hexane-ethyl acetate).
Conditions: See reaction.notes.procedure_details.
Workup: synthesized in Reference Example... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aromatic alcohol | null | null | c1ccc2c(c1)CCC2 | HO- | CCCCCC.C(C)(=O)OCC | null | null | CC(=O)Oc1cc(C)cc2c1CCC2>CCCCCC.C(C)(=O)OCC>Cc1cc(O)c2c(c1)CCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-279fd297f5b14a1c98382efa4fddb87e | CC(C)c1ccc(C(=O)CBr)cc1.Cc1cc(O)cc(C)c1C>>Cc1cc(OCC(=O)c2ccc(C(C)C)cc2)cc(C)c1C | BrCC(=O)C1=CC=C(C=C1)C(C)C.C([O-])([O-])=O.[K+].[K+].O.CC=1C=C(C=C(C1C)C)O>>CC=1C=C(OCC(=O)C2=CC=C(C=C2)C(C)C)C=C(C1C)C | Br[CH2:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([CH:13]([CH3:14])[CH3:15])[cH:16][cH:17]1.[CH3:1][c:2]1[cH:3][c:4]([OH:5])[cH:18][c:19]([CH3:20])[c:21]1[CH3:22]>>[CH3:1][c:2]1[cH:3][c:4]([O:5][CH2:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]([CH:13]([CH3:14])[CH3:15])[cH:16][cH:17]2)[cH:18][c:19]([CH3:20])[c:21]1[CH3:22] | CC(C)c1ccc(C(=O)CBr)cc1.Cc1cc(O)cc(C)c1C | Cc1cc(OCC(=O)c2ccc(C(C)C)cc2)cc(C)c1C | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 8060b8e1565497a5ddf79be1adfe74f552b31798797b8841753247b06bdd2051 | 8749b179916f131d393264a24309227dc6177f560726bed2d1f4567dc2ac63f5 | O=C(COc1ccccc1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:3]=[C:2](-[c:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | 96 | [{"value": 96.0, "product": "CC=1C=C(OCC(=O)C2=CC=C(C=C2)C(C)C)C=C(C1C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Bromo-1-(4-isopropylphenyl)ethanone obtained in Reference Example 164 (20 g, 82.9 mmol) and 3,4,5-trimethylphenol (10.3 g, 75.4 mmol) were added to a solution of potassium carbonate (12.5 g, 90.5 mmol) in acetonitrile solution (200 mL), and mixture was stirred with heating under reflux for 6 hours. The reaction solut... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Aromatic alcohol | Ketone.Ether | null | null | c1ccccc1.c1ccccc1 | HBr | C(C)#N | null | null | CC(C)c1ccc(C(=O)CBr)cc1.Cc1cc(O)cc(C)c1C>C(C)#N>Cc1cc(OCC(=O)c2ccc(C(C)C)cc2)cc(C)c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bfe74ebc06ad485890352a030f64f82c | COc1cc(C(C)C)ccc1C(=O)COc1cc(C)cc(C)c1C>>COc1cc(C(C)C)ccc1-c1coc2c(C)c(C)cc(C)c12 | O.[O-2].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3].C(C)(C)C1=C(C(=CC=C1)OC)C(COC1=C(C(=CC(=C1)C)C)C)=O.C(C)(C)C1=CC(=C(C=C1)C(COC1=C(C(=CC(=C1)C)C)C)=O)OC>>C(C)(C)C1=CC(=C(C=C1)C1=COC2=C1C(=CC(=C2C)C)C)OC | O=[C:12]([c:11]1[c:3]([O:2][CH3:1])[cH:4][c:5]([CH:6]([CH3:7])[CH3:8])[cH:9][cH:10]1)[CH2:13][O:14][c:15]1[c:16]([CH3:17])[c:18]([CH3:19])[cH:20][c:21]([CH3:22])[cH:23]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]([CH3:7])[CH3:8])[cH:9][cH:10][c:11]1-[c:12]1[cH:13][o:14][c:15]2[c:16]([CH3:17])[c:18]([CH3:19])[cH:20][c:21]([C... | COc1cc(C(C)C)ccc1C(=O)COc1cc(C)cc(C)c1C | COc1cc(C(C)C)ccc1-c1coc2c(C)c(C)cc(C)c12 | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 41440ef63bdcad0549de493ff63648d9e9e6255c65e521389e251312ab757f94 | a162075685c9eb50256a00ee0ecfa14ba2a448fd0344b073a356637e7fa80d08 | c1ccc(-c2coc3ccccc23)cc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[O;H0;D2;+0:3]-[c:4](:[c:5]):[cH;D2;+0:6]:[c:7](-[C;D1;H3:8]):[c:9])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13](-[#8:14]):[c:15]>>[#8:14]-[c:13](:[c:15]):[c;H0;D3;+0:10](-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[o;H0;D2;+0:3]:[c:4](:[c:5]):[c;H0;D3;+0:6]:1:[c:7](-[C;D1;H3:8]):[c:9]):[c:11]:[c:12] | 40 | [{"value": 40.0, "product": "C(C)(C)C1=CC(=C(C=C1)C1=COC2=C1C(=CC(=C2C)C)C)OC", "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 5 | HOUR | A mixed solution of the mixture of 1-(2-isopropyl-6-methoxyphenyl)-2-(2,3,5-trimethylphenoxy)ethanone and 1-(4-isopropyl-2-methoxyphenyl)-2-(2,3,5-trimethylphenoxy)ethanone obtained in Reference Example 171 (6.27 g, 19.2 mmol) and Montmorillonite KSF (9.40 g) in toluene (100 mL) was stirred under argon atmosphere at 90... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether | null | c1ccccc1 | c1ccc2occc2c1 | c1ccccc1.c1ccc2occc2c1 | HO- | C1(=CC=CC=C1)C | 90 | 5 | COc1cc(C(C)C)ccc1C(=O)COc1cc(C)cc(C)c1C>C1(=CC=CC=C1)C>COc1cc(C(C)C)ccc1-c1coc2c(C)c(C)cc(C)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-36d699658e99427b8f5cb5a7d0356402 | CC(=O)COc1cc(C)c(Br)c(C)c1Cc1ccc(C(C)C)cc1>>Cc1c(Br)c(C)c2c(C)coc2c1Cc1ccc(C(C)C)cc1 | BrC1=C(C(=C(OCC(=O)C)C=C1C)CC1=CC=C(C=C1)C(C)C)C.CO.C1CCOC1>>BrC=1C(=C(C2=C(C(=CO2)C)C1C)CC1=CC=C(C=C1)C(C)C)C | O=[C:8]([CH3:9])[CH2:10][O:11][c:12]1[cH:7][c:5]([CH3:6])[c:3]([Br:4])[c:2]([CH3:1])[c:13]1[CH2:14][c:15]1[cH:16][cH:17][c:18]([CH:19]([CH3:20])[CH3:21])[cH:22][cH:23]1>>[CH3:1][c:2]1[c:3]([Br:4])[c:5]([CH3:6])[c:7]2[c:8]([CH3:9])[cH:10][o:11][c:12]2[c:13]1[CH2:14][c:15]1[cH:16][cH:17][c:18]([CH:19]([CH3:20])[CH3:21])[... | CC(=O)COc1cc(C)c(Br)c(C)c1Cc1ccc(C(C)C)cc1 | Cc1c(Br)c(C)c2c(C)coc2c1Cc1ccc(C(C)C)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 41440ef63bdcad0549de493ff63648d9e9e6255c65e521389e251312ab757f94 | a162075685c9eb50256a00ee0ecfa14ba2a448fd0344b073a356637e7fa80d08 | c1ccc(Cc2cccc3ccoc23)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH2;D2;+0:3]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8](-[C;D1;H3:9]):[c:10]>>[C;D1;H3:9]-[c:8](:[c:10]):[c;H0;D3;+0:7]1:[c:5](:[c:6]):[o;H0;D2;+0:4]:[cH;D2;+0:3]:[c;H0;D3;+0:1]:1-[C;D1;H3:2] | 84 | [{"value": 84.0, "product": "BrC=1C(=C(C2=C(C(=CO2)C)C1C)CC1=CC=C(C=C1)C(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 1-(4-bromo-1-(2-(4-isopropylbenzyl)-3,5-dimethylphenoxy)acetone obtained in Reference Example 189, the title compound was synthesized in the same manner as in Reference Example 143. Yield 84%. Melting point: 76-77° C. (methanol-THF).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in Reference ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether | null | c1ccccc1 | c1ccc2occc2c1 | c1ccc2occc2c1.c1ccccc1 | HO- | null | null | null | CC(=O)COc1cc(C)c(Br)c(C)c1Cc1ccc(C(C)C)cc1>>Cc1c(Br)c(C)c2c(C)coc2c1Cc1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c45fe905c66147d8b6899abe6b03f83c | Cc1ccc(C(=O)COc2cc(C)cc(C)c2C)cc1>>Cc1ccc(-c2coc3c(C)c(C)cc(C)c23)cc1 | CC1=CC=C(C=C1)C(COC1=C(C(=CC(=C1)C)C)C)=O>>CC1=CC(=C(C2=C1C(=CO2)C2=CC=C(C=C2)C)C)C | O=[C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:19][cH:18]1)[CH2:7][O:8][c:9]1[c:10]([CH3:11])[c:12]([CH3:13])[cH:14][c:15]([CH3:16])[cH:17]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][o:8][c:9]3[c:10]([CH3:11])[c:12]([CH3:13])[cH:14][c:15]([CH3:16])[c:17]23)[cH:18][cH:19]1 | Cc1ccc(C(=O)COc2cc(C)cc(C)c2C)cc1 | Cc1ccc(-c2coc3c(C)c(C)cc(C)c23)cc1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 41440ef63bdcad0549de493ff63648d9e9e6255c65e521389e251312ab757f94 | a162075685c9eb50256a00ee0ecfa14ba2a448fd0344b073a356637e7fa80d08 | c1ccc(-c2coc3ccccc23)cc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[O;H0;D2;+0:3]-[c:4](:[c:5]):[cH;D2;+0:6]:[c:7](-[C;D1;H3:8]):[c:9])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[C;D1;H3:8]-[c:7](:[c:9]):[c;H0;D3;+0:6]1:[c:4](:[c:5]):[o;H0;D2;+0:3]:[cH;D2;+0:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14] | 83 | [{"value": 83.0, "product": "CC1=CC(=C(C2=C1C(=CO2)C2=CC=C(C=C2)C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A mixture of 1-(4-methylphenyl)-2-(2,3,5-trimethylphenoxy)ethanone obtained in Reference Example 163 (1.0 g, 3.73 mmol) and polyphosphoric acid (6.0 g) was stirred at 80° C. for one and half hours. Water was added to the reaction solution, which was extracted with ethyl acetate. The organic layer was washed with a satu... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether | null | c1ccccc1 | c1ccc2occc2c1 | c1ccccc1.c1ccc2occc2c1 | HO- | O | 80 | null | Cc1ccc(C(=O)COc2cc(C)cc(C)c2C)cc1>O>Cc1ccc(-c2coc3c(C)c(C)cc(C)c23)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0f3de572cefc497b89a340b0ddf99649 | Cc1ccc(C(=O)COc2cc(C)cc(C)c2C)nc1>>Cc1ccc(-c2coc3c(C)c(C)cc(C)c23)nc1 | CC=1C=CC(=NC1)C(COC1=C(C(=CC(=C1)C)C)C)=O>>CC=1C=CC(=NC1)C1=COC2=C1C(=CC(=C2C)C)C | O=[C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:19][n:18]1)[CH2:7][O:8][c:9]1[c:10]([CH3:11])[c:12]([CH3:13])[cH:14][c:15]([CH3:16])[cH:17]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][o:8][c:9]3[c:10]([CH3:11])[c:12]([CH3:13])[cH:14][c:15]([CH3:16])[c:17]23)[n:18][cH:19]1 | Cc1ccc(C(=O)COc2cc(C)cc(C)c2C)nc1 | Cc1ccc(-c2coc3c(C)c(C)cc(C)c23)nc1 | null | null | C(C)(=O)OCC.CCCCCC | Aromatic Heterocycle Formation | OtherReaction | 41440ef63bdcad0549de493ff63648d9e9e6255c65e521389e251312ab757f94 | a162075685c9eb50256a00ee0ecfa14ba2a448fd0344b073a356637e7fa80d08 | c1ccc(-c2coc3ccccc23)nc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[O;H0;D2;+0:3]-[c:4](:[c:5]):[cH;D2;+0:6]:[c:7](-[C;D1;H3:8]):[c:9])-[c;H0;D3;+0:10](:[#7;a:11]:[c:12]):[c:13]:[c:14]>>[C;D1;H3:8]-[c:7](:[c:9]):[c;H0;D3;+0:6]1:[c:4](:[c:5]):[o;H0;D2;+0:3]:[cH;D2;+0:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:10](:[#7;a:11]:[c:12]):[c:13]:[c:14] | 87 | [{"value": 87.0, "product": "CC=1C=CC(=NC1)C1=COC2=C1C(=CC(=C2C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 1-(5-methylpyridin-2-yl)-2-(2,3,5-trimethylphenoxy)ethanone obtained in Reference Example 168, the title compound was synthesized in the same manner as in Reference Example 191. Yield 87%. Melting point: 134-135° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in Refe... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether | null | c1ccccc1 | c1ccc2occc2c1 | c1ccncc1.c1ccc2occc2c1 | HO- | C(C)(=O)OCC.CCCCCC | null | null | Cc1ccc(C(=O)COc2cc(C)cc(C)c2C)nc1>C(C)(=O)OCC.CCCCCC>Cc1ccc(-c2coc3c(C)c(C)cc(C)c23)nc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7c6e8c103d3b43209cfdc53cab01544f | Cc1cc2c(c(OCC(=O)c3ccc(C(C)C)cc3)c1)CCC2>>Cc1cc2c(c3occ(-c4ccc(C(C)C)cc4)c13)CCC2 | C(C)(C)C1=CC=C(C=C1)C(COC1=C2CCCC2=CC(=C1)C)=O>>C(C)(C)C1=CC=C(C=C1)C=1C2=C(OC1)C=1CCCC1C=C2C | O=[C:9]([CH2:8][O:7][c:6]1[c:5]2[c:4]([cH:3][c:2]([CH3:1])[cH:19]1)[CH2:22][CH2:21][CH2:20]2)[c:10]1[cH:11][cH:12][c:13]([CH:14]([CH3:15])[CH3:16])[cH:17][cH:18]1>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([c:6]3[o:7][cH:8][c:9](-[c:10]4[cH:11][cH:12][c:13]([CH:14]([CH3:15])[CH3:16])[cH:17][cH:18]4)[c:19]13)[CH2:20][CH2:21][CH2:2... | Cc1cc2c(c(OCC(=O)c3ccc(C(C)C)cc3)c1)CCC2 | Cc1cc2c(c3occ(-c4ccc(C(C)C)cc4)c13)CCC2 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | 93d8e355626b51c3e1420765139d41ff9b8bd96fd39111128004257019275c99 | a162075685c9eb50256a00ee0ecfa14ba2a448fd0344b073a356637e7fa80d08 | c1ccc(-c2coc3c4c(ccc23)CCC4)cc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[O;H0;D2;+0:3]-[c:4](:[c:5]):[cH;D2;+0:6]:[c:7](-[C;D1;H3:8]):[c:9])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[C;D1;H3:8]-[c:7](:[c:9]):[c;H0;D3;+0:6]1:[c:4](:[c:5]):[o;H0;D2;+0:3]:[cH;D2;+0:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14] | 77 | [{"value": 77.0, "product": "C(C)(C)C1=CC=C(C=C1)C=1C2=C(OC1)C=1CCCC1C=C2C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 1-(4-isopropylphenyl)-2-((6-methyl-2,3-dihydro-1H-inden-4-yl)oxy)ethanone obtained in Reference Example 180, the title compound was synthesized in the same manner as in Reference Example 143. Yield 77%. Melting point: 70-72° C. (methanol).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in Refe... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether | null | c1ccc2c(c1)CCC2 | c1cc2ccc3c(c2o1)CCC3 | c1ccccc1.c1cc2ccc3c(c2o1)CCC3 | HO- | CO | null | null | Cc1cc2c(c(OCC(=O)c3ccc(C(C)C)cc3)c1)CCC2>CO>Cc1cc2c(c3occ(-c4ccc(C(C)C)cc4)c13)CCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0789cda7761843f0b7debf893788c792 | CCCC1(CC)COc2c(Cc3ccc(C(C)C)cc3)c(C)cc(C)c21>>CCC1COc2c(Cc3ccc(C(C)C)cc3)c(C)cc(C)c21 | O.C(C)C1(COC2=C1C(=CC(=C2CC2=CC=C(C=C2)C(C)C)C)C)CCC.C(C)[SiH](CC)CC>>C(C)C1COC2=C1C(=CC(=C2CC2=CC=C(C=C2)C(C)C)C)C | CCC[C:3]1([CH2:2][CH3:1])[CH2:4][O:5][c:6]2[c:7]([CH2:8][c:9]3[cH:10][cH:11][c:12]([CH:13]([CH3:14])[CH3:15])[cH:16][cH:17]3)[c:18]([CH3:19])[cH:20][c:21]([CH3:22])[c:23]21>>[CH3:1][CH2:2][CH:3]1[CH2:4][O:5][c:6]2[c:7]([CH2:8][c:9]3[cH:10][cH:11][c:12]([CH:13]([CH3:14])[CH3:15])[cH:16][cH:17]3)[c:18]([CH3:19])[cH:20][c... | CCCC1(CC)COc2c(Cc3ccc(C(C)C)cc3)c(C)cc(C)c21 | CCC1COc2c(Cc3ccc(C(C)C)cc3)c(C)cc(C)c21 | null | null | FC(C(=O)O)(F)F | Miscellaneous | OtherReaction | 3fe279e9a09a7c13f20e636376e4772c519291a99698bd5e669915311127efe2 | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(Cc2cccc3c2OCC3)cc1 | C-C-C-[C;H0;D4;+0:1]1(-[C:2]-[C;D1;H3:3])-[C:4]-[#8:5]-[c:6]:[c:7]-1:[c:8]>>[C;D1;H3:3]-[C:2]-[CH;D3;+0:1]1-[C:4]-[#8:5]-[c:6]:[c:7]-1:[c:8] | 99 | [{"value": 99.0, "product": "C(C)C1COC2=C1C(=CC(=C2CC2=CC=C(C=C2)C(C)C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a mixed solution of 3-ethyl-7-(4-isopropylbenzyl)-4,6-dimethyl-3-propyl-1-benzofuran obtained in Reference Example 183 (941 mg, 2.94 mmol) in trifluoroacetic acid (5 mL) was added dropwise triethylsilane (0.94 mL, 5.87 mmol), and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | Other | FC(C(=O)O)(F)F | null | 1 | CCCC1(CC)COc2c(Cc3ccc(C(C)C)cc3)c(C)cc(C)c21>FC(C(=O)O)(F)F>CCC1COc2c(Cc3ccc(C(C)C)cc3)c(C)cc(C)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0e94bfb60f1e4b088e4f3009fa21349d | COc1cc(C(C)C)ccc1-c1coc2c(C)c(C)cc(C)c12>>COc1cc(C(C)C)ccc1C1COc2c(C)c(C)cc(C)c21 | C(C)(C)C1=CC(=C(C=C1)C1=COC2=C1C(=CC(=C2C)C)C)OC>>C(C)(C)C1=CC(=C(C=C1)C1COC2=C1C(=CC(=C2C)C)C)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]([CH3:7])[CH3:8])[cH:9][cH:10][c:11]1-[c:12]1[cH:13][o:14][c:15]2[c:16]([CH3:17])[c:18]([CH3:19])[cH:20][c:21]([CH3:22])[c:23]12>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]([CH3:7])[CH3:8])[cH:9][cH:10][c:11]1[CH:12]1[CH2:13][O:14][c:15]2[c:16]([CH3:17])[c:18]([CH3:19])[cH:20][c:21]([CH3:2... | COc1cc(C(C)C)ccc1-c1coc2c(C)c(C)cc(C)c12 | COc1cc(C(C)C)ccc1C1COc2c(C)c(C)cc(C)c21 | null | null | CO | Reduction | OtherReaction | b86bd3f15ad056b18f24f98e80df6dc8108bba5322ef4250b69a51408c14b3cb | 7ece147c6909fe307632f67c21e1517a1747c8ff389dff4b19e644c711d1d84d | c1ccc(C2COc3ccccc32)cc1 | [#8:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[o;H0;D2;+0:7]:[c:8](:[c:9]):[c:10]:1:[c:11]):[c:12]:[c:13]>>[#8:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[CH;D3;+0:5]1-[CH2;D2;+0:6]-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]-1:[c:11]):[c:12]:[c:13] | 79 | [{"value": 79.0, "product": "C(C)(C)C1=CC(=C(C=C1)C1COC2=C1C(=CC(=C2C)C)C)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3-(4-isopropyl-2-methoxyphenyl)-4,6,7-trimethyl-1-benzofuran obtained in Reference Example 188, the title compound was synthesized in the same manner as in Reference Example 199. Yield 79%. Melting point: 102-103° C. (methanol).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in Reference Examp... | 10.6084/m9.figshare.5104873.v1 | null | null | Ether | c1ccc2occc2c1 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | null | CO | null | null | COc1cc(C(C)C)ccc1-c1coc2c(C)c(C)cc(C)c12>CO>COc1cc(C(C)C)ccc1C1COc2c(C)c(C)cc(C)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-979d94150877408c8160042ecebf09e9 | Cc1ccc(-c2coc3c(C)c(C)cc(C)c23)nc1>>Cc1ccc(C2COc3c(C)c(C)cc(C)c32)nc1 | CC=1C=CC(=NC1)C1=COC2=C1C(=CC(=C2C)C)C>>CC=1C=CC(=NC1)C1COC2=C1C(=CC(=C2C)C)C | [CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][o:8][c:9]3[c:10]([CH3:11])[c:12]([CH3:13])[cH:14][c:15]([CH3:16])[c:17]23)[n:18][cH:19]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]2[CH2:7][O:8][c:9]3[c:10]([CH3:11])[c:12]([CH3:13])[cH:14][c:15]([CH3:16])[c:17]32)[n:18][cH:19]1 | Cc1ccc(-c2coc3c(C)c(C)cc(C)c23)nc1 | Cc1ccc(C2COc3c(C)c(C)cc(C)c32)nc1 | null | null | CO | Reduction | OtherReaction | b86bd3f15ad056b18f24f98e80df6dc8108bba5322ef4250b69a51408c14b3cb | 7ece147c6909fe307632f67c21e1517a1747c8ff389dff4b19e644c711d1d84d | c1ccc(C2COc3ccccc32)nc1 | [c:1]:[c:2]1:[o;H0;D2;+0:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:6](:[#7;a:7]:[c:8]):[c:9]:[c:10]):[c:11]:1:[c:12]>>[c:1]:[c:2]1:[c:11](:[c:12])-[CH;D3;+0:5](-[c;H0;D3;+0:6](:[#7;a:7]:[c:8]):[c:9]:[c:10])-[CH2;D2;+0:4]-[O;H0;D2;+0:3]-1 | 89 | [{"value": 89.0, "product": "CC=1C=CC(=NC1)C1COC2=C1C(=CC(=C2C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 5-methyl-2-(4,6,7-trimethyl-1-benzofuran-3-yl)pyridine obtained in Reference Example 192, the title compound was synthesized in the same manner as in Reference Example 144. Yield 89%. Melting point: 69-70° C. (methanol).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in Reference Example 192 | 10.6084/m9.figshare.5104873.v1 | null | null | Ether | c1ccc2occc2c1 | c1ccc2c(c1)CCO2 | c1ccncc1.c1ccc2c(c1)CCO2 | null | CO | null | null | Cc1ccc(-c2coc3c(C)c(C)cc(C)c23)nc1>CO>Cc1ccc(C2COc3c(C)c(C)cc(C)c32)nc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1507f54fa3714afcbb767b79755eb5f1 | Cc1cc2occ(-c3ccc(C(C)C)cc3)c2c(C)c1C>>Cc1cc2c(c(C)c1C)C(c1ccc(C(C)C)cc1)CO2 | C(C)(C)C1=CC=C(C=C1)C1=COC2=C1C(=C(C(=C2)C)C)C>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2)C)C)C | [CH3:1][c:2]1[cH:3][c:4]2[c:5]([c:6]([CH3:7])[c:8]1[CH3:9])[c:10](-[c:11]1[cH:12][cH:13][c:14]([CH:15]([CH3:16])[CH3:17])[cH:18][cH:19]1)[cH:20][o:21]2>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([c:6]([CH3:7])[c:8]1[CH3:9])[CH:10]([c:11]1[cH:12][cH:13][c:14]([CH:15]([CH3:16])[CH3:17])[cH:18][cH:19]1)[CH2:20][O:21]2 | Cc1cc2occ(-c3ccc(C(C)C)cc3)c2c(C)c1C | Cc1cc2c(c(C)c1C)C(c1ccc(C(C)C)cc1)CO2 | null | null | CO | Reduction | OtherReaction | b86bd3f15ad056b18f24f98e80df6dc8108bba5322ef4250b69a51408c14b3cb | 7ece147c6909fe307632f67c21e1517a1747c8ff389dff4b19e644c711d1d84d | c1ccc(C2COc3ccccc32)cc1 | [c:1]:[c:2]:[c;H0;D3;+0:3](-[c;H0;D3;+0:4]1:[cH;D2;+0:5]:[o;H0;D2;+0:6]:[c:7](:[c:8]):[c:9]:1:[c:10]):[c:11]:[c:12]>>[c:1]:[c:2]:[c;H0;D3;+0:3](-[CH;D3;+0:4]1-[CH2;D2;+0:5]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]-1:[c:10]):[c:11]:[c:12] | 74 | [{"value": 74.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2)C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3-(4-isopropylphenyl)-4,5,6-trimethyl-1-benzofuran obtained in Reference Example 194, the title compound was synthesized in the same manner as in Reference Example 199. Yield 74%. Melting point: 70-71° C. (methanol).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in Reference Example 194 | 10.6084/m9.figshare.5104873.v1 | null | null | Ether | c1ccc2occc2c1 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | null | CO | null | null | Cc1cc2occ(-c3ccc(C(C)C)cc3)c2c(C)c1C>CO>Cc1cc2c(c(C)c1C)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-54ba32d94e3c4e78b9dd43e59305d043 | CC(=O)Oc1c(C)c2c(-c3ccc(C(C)C)cc3)coc2c2ccccc12>>CC(=O)Oc1c(C)c2c(c3ccccc13)OCC2c1ccc(C(C)C)cc1 | C(C)(=O)OC1=C(C2=C(OC=C2C2=CC=C(C=C2)C(C)C)C2=CC=CC=C12)C>>C(C)(=O)OC1=C(C2=C(OCC2C2=CC=C(C=C2)C(C)C)C2=CC=CC=C12)C | [CH3:1][C:2](=[O:3])[O:4][c:5]1[c:6]([CH3:7])[c:8]2[c:9]([c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]13)[o:16][cH:17][c:18]2-[c:19]1[cH:20][cH:21][c:22]([CH:23]([CH3:24])[CH3:25])[cH:26][cH:27]1>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[c:6]([CH3:7])[c:8]2[c:9]([c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]13)[O:16][CH2:17][CH:18]2[c:1... | CC(=O)Oc1c(C)c2c(-c3ccc(C(C)C)cc3)coc2c2ccccc12 | CC(=O)Oc1c(C)c2c(c3ccccc13)OCC2c1ccc(C(C)C)cc1 | null | null | CCCCCC.C(C)(=O)OCC | Reduction | OtherReaction | c5d6a931bde9ee05f703d9f3bb0dea434cc495387a68ac11712312e97be0219d | 7ece147c6909fe307632f67c21e1517a1747c8ff389dff4b19e644c711d1d84d | c1ccc(C2COc3c2ccc2ccccc32)cc1 | [c:1]:[c:2]1:[o;H0;D2;+0:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:11]:1:[c:12]>>[c:1]:[c:2]1:[c:11](:[c:12])-[CH;D3;+0:5](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10])-[CH2;D2;+0:4]-[O;H0;D2;+0:3]-1 | 74 | [{"value": 74.0, "product": "C(C)(=O)OC1=C(C2=C(OCC2C2=CC=C(C=C2)C(C)C)C2=CC=CC=C12)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3-(4-isopropylphenyl)-4-methylnaphtho[1,2-b]furan-5-yl acetate obtained in Reference Example 195, the title compound was synthesized in the same manner as in Reference Example 199. Yield 74%. Melting point: 109-110° C. (hexane-ethyl acetate).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in R... | 10.6084/m9.figshare.5104873.v1 | null | null | Ether | c1ccc2c(c1)ccc1ccoc12 | c1ccc2c3c(ccc2c1)CCO3 | c1ccc2c3c(ccc2c1)CCO3.c1ccccc1 | null | CCCCCC.C(C)(=O)OCC | null | null | CC(=O)Oc1c(C)c2c(-c3ccc(C(C)C)cc3)coc2c2ccccc12>CCCCCC.C(C)(=O)OCC>CC(=O)Oc1c(C)c2c(c3ccccc13)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-36a4407a10f24972b36bfd2da0fe9688 | Cc1cc2c(c3occ(-c4ccc(C(C)C)cc4)c13)CCCC2>>Cc1cc2c(c3c1C(c1ccc(C(C)C)cc1)CO3)CCCC2 | C(C)(C)C1=CC=C(C=C1)C=1C2=C(OC1)C=1CCCCC1C=C2C>>C(C)(C)C1=CC=C(C=C1)C1C2=C(OC1)C=1CCCCC1C=C2C | [CH3:1][c:2]1[cH:3][c:4]2[c:5]([c:6]3[c:7]1[c:8](-[c:9]1[cH:10][cH:11][c:12]([CH:13]([CH3:14])[CH3:15])[cH:16][cH:17]1)[cH:18][o:19]3)[CH2:20][CH2:21][CH2:22][CH2:23]2>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([c:6]3[c:7]1[CH:8]([c:9]1[cH:10][cH:11][c:12]([CH:13]([CH3:14])[CH3:15])[cH:16][cH:17]1)[CH2:18][O:19]3)[CH2:20][CH2:21]... | Cc1cc2c(c3occ(-c4ccc(C(C)C)cc4)c13)CCCC2 | Cc1cc2c(c3c1C(c1ccc(C(C)C)cc1)CO3)CCCC2 | null | null | CO | Reduction | OtherReaction | 29fcf10dd290728648b93ad69539e92429cd27b9d1d71b828805735f622a4123 | 7ece147c6909fe307632f67c21e1517a1747c8ff389dff4b19e644c711d1d84d | c1ccc(C2COc3c2ccc2c3CCCC2)cc1 | [c:1]:[c:2]:[c;H0;D3;+0:3](-[c;H0;D3;+0:4]1:[cH;D2;+0:5]:[o;H0;D2;+0:6]:[c:7](:[c:8]):[c:9]:1:[c:10]):[c:11]:[c:12]>>[c:1]:[c:2]:[c;H0;D3;+0:3](-[CH;D3;+0:4]1-[CH2;D2;+0:5]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]-1:[c:10]):[c:11]:[c:12] | 80 | [{"value": 80.0, "product": "C(C)(C)C1=CC=C(C=C1)C1C2=C(OC1)C=1CCCCC1C=C2C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3-(4-isopropylphenyl)-4-methyl-6,7,8,9-tetrahydronaphtho[1,2-b]furan obtained in Reference Example 196, the title compound was synthesized in the same manner as in Reference Example 199. Yield 80%. Melting point: 54-55° C. (methanol).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in Reference... | 10.6084/m9.figshare.5104873.v1 | null | null | Ether | c1cc2ccc3c(c2o1)CCCC3 | c1cc2c(c3c1CCCC3)OCC2 | c1ccccc1.c1cc2c(c3c1CCCC3)OCC2 | null | CO | null | null | Cc1cc2c(c3occ(-c4ccc(C(C)C)cc4)c13)CCCC2>CO>Cc1cc2c(c3c1C(c1ccc(C(C)C)cc1)CO3)CCCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-967359f5925445a5bd2eed8f93e9f159 | Cc1cc2c(c3occ(-c4ccc(C(C)C)cc4)c13)CCC2>>Cc1cc2c(c3c1C(c1ccc(C(C)C)cc1)CO3)CCC2 | C(C)(C)C1=CC=C(C=C1)C=1C2=C(OC1)C=1CCCC1C=C2C>>C(C)(C)C1=CC=C(C=C1)C1C2=C(OC1)C=1CCCC1C=C2C | [CH3:1][c:2]1[cH:3][c:4]2[c:5]([c:6]3[c:7]1[c:8](-[c:9]1[cH:10][cH:11][c:12]([CH:13]([CH3:14])[CH3:15])[cH:16][cH:17]1)[cH:18][o:19]3)[CH2:20][CH2:21][CH2:22]2>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([c:6]3[c:7]1[CH:8]([c:9]1[cH:10][cH:11][c:12]([CH:13]([CH3:14])[CH3:15])[cH:16][cH:17]1)[CH2:18][O:19]3)[CH2:20][CH2:21][CH2:22]... | Cc1cc2c(c3occ(-c4ccc(C(C)C)cc4)c13)CCC2 | Cc1cc2c(c3c1C(c1ccc(C(C)C)cc1)CO3)CCC2 | null | null | CO | Reduction | OtherReaction | 4cc5989d75a872b3def1d2af6752bd9192681dbd447c8f5ec9b435b547fb5cde | 7ece147c6909fe307632f67c21e1517a1747c8ff389dff4b19e644c711d1d84d | c1ccc(C2COc3c2ccc2c3CCC2)cc1 | [c:1]:[c:2]:[c;H0;D3;+0:3](-[c;H0;D3;+0:4]1:[cH;D2;+0:5]:[o;H0;D2;+0:6]:[c:7](:[c:8]):[c:9]:1:[c:10]):[c:11]:[c:12]>>[c:1]:[c:2]:[c;H0;D3;+0:3](-[CH;D3;+0:4]1-[CH2;D2;+0:5]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]-1:[c:10]):[c:11]:[c:12] | 59 | [{"value": 59.0, "product": "C(C)(C)C1=CC=C(C=C1)C1C2=C(OC1)C=1CCCC1C=C2C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3-(4-isopropylphenyl)-4-methyl-7,8-dihydro-6H-indeno[4,5-b]furan obtained in Reference Example 197, the title compound was synthesized in the same manner as in Reference Example 199. Yield 59%. Melting point: 77-78° C. (methanol).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in Reference Exa... | 10.6084/m9.figshare.5104873.v1 | null | null | Ether | c1cc2ccc3c(c2o1)CCC3 | c1cc2c(c3c1CCC3)OCC2 | c1ccccc1.c1cc2c(c3c1CCC3)OCC2 | null | CO | null | null | Cc1cc2c(c3occ(-c4ccc(C(C)C)cc4)c13)CCC2>CO>Cc1cc2c(c3c1C(c1ccc(C(C)C)cc1)CO3)CCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-376884f57c6042b485126ed4b1724381 | Cc1cc(C)c2c(-c3ccc(C(C)C)cc3)csc2c1>>Cc1cc(C)c2c(c1)SCC2c1ccc(C(C)C)cc1 | C(C)(C)C1=CC=C(C=C1)C1=CSC2=C1C(=CC(=C2)C)C>>C(C)(C)C1=CC=C(C=C1)C1CSC2=C1C(=CC(=C2)C)C | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:7]([cH:8]1)[s:9][cH:10][c:11]2-[c:12]1[cH:13][cH:14][c:15]([CH:16]([CH3:17])[CH3:18])[cH:19][cH:20]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:7]([cH:8]1)[S:9][CH2:10][CH:11]2[c:12]1[cH:13][cH:14][c:15]([CH:16]([CH3:17])[CH3:18])[cH:19][cH:20]1 | Cc1cc(C)c2c(-c3ccc(C(C)C)cc3)csc2c1 | Cc1cc(C)c2c(c1)SCC2c1ccc(C(C)C)cc1 | null | null | CO | Reduction | OtherReaction | 81b10a55828621648238065e242c08be60fa60eacb706df67763367a601a204b | 6494b79298919cfd71fc3b54c2d8d5548ad70aacbcfe4bc3563445f4ace326cc | c1ccc(C2CSc3ccccc32)cc1 | [c:1]:[c:2]:[c;H0;D3;+0:3](-[c;H0;D3;+0:4]1:[cH;D2;+0:5]:[s;H0;D2;+0:6]:[c:7](:[c:8]):[c:9]:1:[c:10]):[c:11]:[c:12]>>[c:1]:[c:2]:[c;H0;D3;+0:3](-[CH;D3;+0:4]1-[CH2;D2;+0:5]-[S;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]-1:[c:10]):[c:11]:[c:12] | 85 | [{"value": 85.0, "product": "C(C)(C)C1=CC=C(C=C1)C1CSC2=C1C(=CC(=C2)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3-(4-isopropylphenyl)-4,6-dimethyl-1-benzothiophene obtained in Reference Example 198, the title compound was synthesized in the same manner as in Reference Example 199. Yield 85%. Melting point: 74-75° C. (methanol).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in Reference Example 198 | 10.6084/m9.figshare.5104873.v1 | null | null | Monosulfide | c1ccc2sccc2c1 | c1ccc2c(c1)CCS2 | c1ccc2c(c1)CCS2.c1ccccc1 | null | CO | null | null | Cc1cc(C)c2c(-c3ccc(C(C)C)cc3)csc2c1>CO>Cc1cc(C)c2c(c1)SCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-af23777cc5614e6ba9b4860456136b7b | C=CCBr.Cc1cc(C)cc(O)c1>>C=CCOc1cc(C)cc(C)c1 | CC=1C=C(C=C(C1)C)O.C(C=C)Br>>C(C=C)OC1=CC(=CC(=C1)C)C | Br[CH2:3][CH:2]=[CH2:1].[OH:4][c:5]1[cH:6][c:7]([CH3:8])[cH:9][c:10]([CH3:11])[cH:12]1>>[CH2:1]=[CH:2][CH2:3][O:4][c:5]1[cH:6][c:7]([CH3:8])[cH:9][c:10]([CH3:11])[cH:12]1 | C=CCBr.Cc1cc(C)cc(O)c1 | C=CCOc1cc(C)cc(C)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H2:3]=[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 78 | [{"value": 78.0, "product": "C(C=C)OC1=CC(=CC(=C1)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3,5-dimethylphenol and allyl bromide, the title compound was synthesized in the same manner as in Reference Example 213. Yield 78%. Oily matter.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | null | null | null | C=CCBr.Cc1cc(C)cc(O)c1>>C=CCOc1cc(C)cc(C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2d45c89bf97c4e4384b04b3d4a5a80aa | C=CCOc1cc(C)cc(C)c1>>C=CCc1c(C)cc(C)cc1O | C(C)N(C1=CC=CC=C1)CC.C(C=C)OC1=CC(=CC(=C1)C)C.C(C)(=O)OCC>>C(C=C)C1=C(C=C(C=C1C)C)O | [CH2:1]=[CH:2][CH2:3][O:12][c:11]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([CH3:9])[cH:10]1>>[CH2:1]=[CH:2][CH2:3][c:4]1[c:5]([CH3:6])[cH:7][c:8]([CH3:9])[cH:10][c:11]1[OH:12] | C=CCOc1cc(C)cc(C)c1 | C=CCc1c(C)cc(C)cc1O | null | null | null | Miscellaneous | OtherReaction | f9046ab8287acad6d9b914f5f533866252d6845a323cc2516eb4a5b1de541a76 | 58578155da4647eafb0f18a2061753170490dc4f2b17890a513522e28d385731 | c1ccccc1 | [C;D1;H2:1]=[C:2]-[CH2;D2;+0:3]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8](-[C;D1;H3:9]):[c:10]>>[C;D1;H2:1]=[C:2]-[CH2;D2;+0:3]-[c;H0;D3;+0:7](:[c:5](-[OH;D1;+0:4]):[c:6]):[c:8](-[C;D1;H3:9]):[c:10] | 94 | [{"value": 94.0, "product": "C(C=C)C1=C(C=C(C=C1C)C)O", "details": "PERCENTYIELD", "is_desired": false}] | 210 | CELSIUS | 5 | HOUR | A solution of 1-(allyloxy)-3,5-dimethylbenzene obtained in Reference Example 214 (1.0 g, 6.2 mmol) in N,N-diethylaniline (4 mL) was stirred under argon atmosphere at 210° C. for 5 hours. To the reaction solution was added ethyl acetate, and the mixture was washed with hydrochloric acid and a saturated brine, dried over... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Allyl | Aromatic alcohol.Allyl | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | null | 210 | 5 | C=CCOc1cc(C)cc(C)c1>>C=CCc1c(C)cc(C)cc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b2e44f61ff3b4d15998e9034f5bbe715 | C=CCc1c(C)cc(C)cc1O>>Cc1cc(C)c2c(c1)OC(C)C2 | [OH-].[Na+].C(C=C)C1=C(C=C(C=C1C)C)O.Cl>>CC1OC2=C(C1)C(=CC(=C2)C)C | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([CH2:12][CH:10]=[CH2:11])[c:7]([OH:9])[cH:8]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:7]([cH:8]1)[O:9][CH:10]([CH3:11])[CH2:12]2 | C=CCc1c(C)cc(C)cc1O | Cc1cc(C)c2c(c1)OC(C)C2 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | c203e84217e22245846e4c6a724dfb0e4e73ba54c7c1c26a5c96843972d34e3f | 2cf6238897596721476a23e3f72d55bb9c387a1a2bac9341b03b1d7e520c494f | c1ccc2c(c1)CCO2 | [CH2;D1;+0:1]=[CH;D2;+0:2]-[C:3]-[c:4]:[c:5](-[OH;D1;+0:6]):[c:7]>>[CH3;D1;+0:1]-[CH;D3;+0:2]1-[C:3]-[c:4]:[c:5](:[c:7])-[O;H0;D2;+0:6]-1 | 50 | [{"value": 50.0, "product": "CC1OC2=C(C1)C(=CC(=C2)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2-allyl-3,5-dimethylphenol obtained in Reference Example 215 (935 mg, 5.77 mmol) in methanol (5 mL) was added concentrated hydrochloric acid (5 mL), and the mixture was heated under reflux under argon atmosphere for 20 hours. The reaction solution was neutralized by aqueous sodium hydroxide solution, w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Allyl | Ether | null | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | null | CO | null | null | C=CCc1c(C)cc(C)cc1O>CO>Cc1cc(C)c2c(c1)OC(C)C2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d299f0c33a3c418e8423bb0c427f819e | Cc1cc(C)c(Br)c(O)c1.ClCCCl>>CC1=CC(C)(OCCCl)C(Br)C=C1 | ClCCCl.BrC1=C(C=C(C=C1C)C)O.[OH-].[Na+].O.O>>BrC1C(C=C(C=C1)C)(C)OCCCl | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:10]([Br:11])[c:12]([OH:6])[cH:13]1.Cl[CH2:7][CH2:8][Cl:9]>>[CH3:1][C:2]1=[CH:3][C:4]([CH3:5])([O:6][CH2:7][CH2:8][Cl:9])[CH:10]([Br:11])[CH:12]=[CH:13]1 | Cc1cc(C)c(Br)c(O)c1.ClCCCl | CC1=CC(C)(OCCCl)C(Br)C=C1 | null | [Cl-].C(C1=CC=CC=C1)[N+](CCCC)(CCCC)CCCC | null | Heteroatom Alkylation and Arylation | OtherReaction | 8a87e41f769508f5f72feb1e921dcab2360164e40b08c458773b5f065ad05d13 | 75d3f7ba8c0b0a4a4879dd7f6d81c618f4b895e454bfe38fa3fb8cd3d3943b95 | C1=CCCC=C1 | Cl-[CH2;D2;+0:1]-[C:2]-[Cl;D1;H0:3].[Br;D1;H0:4]-[c;H0;D3;+0:5]1:[c;H0;D3;+0:6](-[OH;D1;+0:7]):[cH;D2;+0:8]:[c;H0;D3;+0:9](-[C;D1;H3:10]):[cH;D2;+0:11]:[c;H0;D3;+0:12]:1-[C;D1;H3:13]>>[Br;D1;H0:4]-[CH;D3;+0:5]1-[CH;D2;+0:6]=[CH;D2;+0:8]-[C;H0;D3;+0:9](-[C;D1;H3:10])=[CH;D2;+0:11]-[C;H0;D4;+0:12]-1(-[C;D1;H3:13])-[O;H0;... | 90 | [{"value": 90.0, "product": "BrC1C(C=C(C=C1)C)(C)OCCCl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixed solution of 2-bromo-3,5-dimethylphenol obtained in Reference Example 149 (16.3 g, 74.6 mmol) and benzyl-tri-n-butylammonium chloride (23.3 g, 7.46 mmol) in 1,2-dichloroethane (150 mL)—a 8 N aqueous sodium hydroxide solution (26 mL)—water (110 mL), was heated under reflux for 5 hours. Water was added to the reac... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide.Aromatic alcohol | Secondary halide.Ether | c1ccccc1 | C1=CCCC=C1 | C1=CCCC=C1 | Other | [Cl-].C(C1=CC=CC=C1)[N+](CCCC)(CCCC)CCCC | null | null | Cc1cc(C)c(Br)c(O)c1.ClCCCl>[Cl-].C(C1=CC=CC=C1)[N+](CCCC)(CCCC)CCCC>CC1=CC(C)(OCCCl)C(Br)C=C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4069b5c34ce74785952f8b647c2468df | CC1=CC(C)(OCCCl)C(Br)C=C1>>Cc1cc(C)c2c(c1)OCC2 | BrC1C(C=C(C=C1)C)(C)OCCCl.C(CCC)[Li]>>CC1=CC(=CC2=C1CCO2)C | Cl[CH2:11][CH2:10][O:9][C:7]1([CH3:5])[CH:6](Br)[CH:4]=[CH:3][C:2]([CH3:1])=[CH:8]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:7]([cH:8]1)[O:9][CH2:10][CH2:11]2 | CC1=CC(C)(OCCCl)C(Br)C=C1 | Cc1cc(C)c2c(c1)OCC2 | null | null | C1CCOC1 | Reduction | OtherReaction | e79da9d17b9a7e30a45befadee20cabcae16328f6efdc6e9f0986edd108c8779 | 8116179373324ade3cce08d6faafa5b99519b8c2787b147854493a3e76a4344f | c1ccc2c(c1)CCO2 | Br-[CH;D3;+0:1]1-[CH;D2;+0:2]=[CH;D2;+0:3]-[C;H0;D3;+0:4](-[C;D1;H3:5])=[CH;D2;+0:6]-[C;H0;D4;+0:7]-1(-[CH3;D1;+0:8])-[#8:9]-[C:10]-[CH2;D2;+0:11]-Cl>>[C;D1;H3:5]-[c;H0;D3;+0:4]1:[cH;D2;+0:3]:[c;H0;D3;+0:2](-[CH3;D1;+0:8]):[c;H0;D3;+0:1]2:[c;H0;D3;+0:7](:[cH;D2;+0:6]:1)-[#8:9]-[C:10]-[CH2;D2;+0:11]-2 | 96 | [{"value": 96.0, "product": "CC1=CC(=CC2=C1CCO2)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 1-bromo-2-(2-chloroethoxy)-2,4-dimethylbenzene obtained in Reference Example 217 (8.70 g, 33.0 mmol) in THF (210 mL) was quickly added n-butyllithium (1.6 M hexane solution, 31 mL, 49.5 mmol) under argon atmosphere at 0° C., and the mixture was stirred for 30 minutes. The reaction solution was warmed t... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Primary halide.Ether | Ether | C1=CCCC=C1 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | HCl.Br- | C1CCOC1 | null | 0.5 | CC1=CC(C)(OCCCl)C(Br)C=C1>C1CCOC1>Cc1cc(C)c2c(c1)OCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2406c50f42984f69a1fee41857fc5967 | Cc1cc(C)c(C)c(O)c1.O=C(O)C(O)c1ccccc1>>Cc1cc(C)c2c(c1C)OC(=O)C2c1ccccc1 | CC1=C(C=C(C=C1C)C)O.OC(C(=O)O)C1=CC=CC=C1>>C1(=CC=CC=C1)C1C(OC2=C1C(=CC(=C2C)C)C)=O | O[c:7]1[c:6]([CH3:9])[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:8]1.O[CH:13]([C:11]([OH:10])=[O:12])[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:7]([c:8]1[CH3:9])[O:10][C:11](=[O:12])[CH:13]2[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | Cc1cc(C)c(C)c(O)c1.O=C(O)C(O)c1ccccc1 | Cc1cc(C)c2c(c1C)OC(=O)C2c1ccccc1 | null | null | C(C)(=O)OCC.CCCCCC | Heteroatom Alkylation and Arylation | OtherReaction | a36a17d3b5a98a14927a5ab2b0be42d209b866ef66a0bb2bbf9dcb43cad4f8d7 | 908e0f9e50a05a6374ff137c29a63b494c9fdcd7afae396ae828385ea73c4999 | O=C1Oc2ccccc2C1c1ccccc1 | O-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4])-[c:5](:[c:6]):[c:7].O-[c;H0;D3;+0:8]1:[cH;D2;+0:9]:[c:10](-[C;D1;H3:11]):[c:12]:[c:13](-[C;D1;H3:14]):[c;H0;D3;+0:15]:1-[CH3;D1;+0:16]>>[C;D1;H3:11]-[c:10]1:[c:12]:[c:13](-[C;D1;H3:14]):[c;H0;D3;+0:15]2:[c;H0;D3;+0:8](:[c;H0;D3;+0:9]:1-[CH3;D1;+0:16])-[O;H0;D2;+0:4]-[C:... | 37 | [{"value": 37.0, "product": "C1(=CC=CC=C1)C1C(OC2=C1C(=CC(=C2C)C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2,3,5-trimethylphenol and hydroxy(phenyl)acetic acid, the title compound was synthesized in the same manner as in Reference Example 2. Yield 37%. Melting point: 129-130° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary alcohol.Aromatic alcohol | Ester | c1ccccc1 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | HO- | C(C)(=O)OCC.CCCCCC | null | null | Cc1cc(C)c(C)c(O)c1.O=C(O)C(O)c1ccccc1>C(C)(=O)OCC.CCCCCC>Cc1cc(C)c2c(c1C)OC(=O)C2c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d0bc8a486bf34fbfb293952e63d1b3ab | Cc1cc(C)c(C)c(O)c1.O=C(O)C(O)c1ccc(Br)cc1>>Cc1cc(C)c2c(c1C)OC(=O)C2c1ccc(Br)cc1 | CC1=C(C=C(C=C1C)C)O.OC(C(=O)O)C1=CC=C(C=C1)Br>>BrC1=CC=C(C=C1)C1C(OC2=C1C(=CC(=C2C)C)C)=O | O[c:7]1[c:6]([CH3:9])[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:8]1.O[CH:13]([C:11]([OH:10])=[O:12])[c:14]1[cH:15][cH:16][c:17]([Br:18])[cH:19][cH:20]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:7]([c:8]1[CH3:9])[O:10][C:11](=[O:12])[CH:13]2[c:14]1[cH:15][cH:16][c:17]([Br:18])[cH:19][cH:20]1 | Cc1cc(C)c(C)c(O)c1.O=C(O)C(O)c1ccc(Br)cc1 | Cc1cc(C)c2c(c1C)OC(=O)C2c1ccc(Br)cc1 | null | null | C(C)(=O)OCC.CCCCCC | Heteroatom Alkylation and Arylation | OtherReaction | a36a17d3b5a98a14927a5ab2b0be42d209b866ef66a0bb2bbf9dcb43cad4f8d7 | 908e0f9e50a05a6374ff137c29a63b494c9fdcd7afae396ae828385ea73c4999 | O=C1Oc2ccccc2C1c1ccccc1 | O-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4])-[c:5](:[c:6]):[c:7].O-[c;H0;D3;+0:8]1:[cH;D2;+0:9]:[c:10](-[C;D1;H3:11]):[c:12]:[c:13](-[C;D1;H3:14]):[c;H0;D3;+0:15]:1-[CH3;D1;+0:16]>>[C;D1;H3:11]-[c:10]1:[c:12]:[c:13](-[C;D1;H3:14]):[c;H0;D3;+0:15]2:[c;H0;D3;+0:8](:[c;H0;D3;+0:9]:1-[CH3;D1;+0:16])-[O;H0;D2;+0:4]-[C:... | 43 | [{"value": 43.0, "product": "BrC1=CC=C(C=C1)C1C(OC2=C1C(=CC(=C2C)C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2,3,5-trimethylphenol and hydroxy(4-bromophenyl)acetic acid, the title compound was synthesized in the same manner as in Reference Example 2. Yield 43%. Melting point: 168-169° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary alcohol.Aromatic alcohol | Ester | c1ccccc1 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | HO- | C(C)(=O)OCC.CCCCCC | null | null | Cc1cc(C)c(C)c(O)c1.O=C(O)C(O)c1ccc(Br)cc1>C(C)(=O)OCC.CCCCCC>Cc1cc(C)c2c(c1C)OC(=O)C2c1ccc(Br)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cc683a799c084f41bca172646b3cd04b | CC(C)c1ccc(C(O)C(=O)O)cc1.Cc1ccc(C)c(O)c1>>Cc1ccc(C)c2c1OC(=O)C2c1ccc(C(C)C)cc1 | OC(C(=O)O)C1=CC=C(C=C1)C(C)C.CC1=C(C=C(C=C1)C)O>>C(C)(C)C1=CC=C(C=C1)C1C(OC2=C1C(=CC=C2C)C)=O | O[CH:12]([C:10]([OH:9])=[O:11])[c:13]1[cH:14][cH:15][c:16]([CH:17]([CH3:18])[CH3:19])[cH:20][cH:21]1.O[c:7]1[c:5]([CH3:6])[cH:4][cH:3][c:2]([CH3:1])[cH:8]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH3:6])[c:7]2[c:8]1[O:9][C:10](=[O:11])[CH:12]2[c:13]1[cH:14][cH:15][c:16]([CH:17]([CH3:18])[CH3:19])[cH:20][cH:21]1 | CC(C)c1ccc(C(O)C(=O)O)cc1.Cc1ccc(C)c(O)c1 | Cc1ccc(C)c2c1OC(=O)C2c1ccc(C(C)C)cc1 | null | null | CCCCCC.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | a36a17d3b5a98a14927a5ab2b0be42d209b866ef66a0bb2bbf9dcb43cad4f8d7 | 908e0f9e50a05a6374ff137c29a63b494c9fdcd7afae396ae828385ea73c4999 | O=C1Oc2ccccc2C1c1ccccc1 | O-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4])-[c:5](:[c:6]):[c:7].O-[c;H0;D3;+0:8]1:[cH;D2;+0:9]:[c:10](-[C;D1;H3:11]):[c:12]:[c:13]:[c:14]:1-[C;D1;H3:15]>>[C;D1;H3:11]-[c:10]1:[c:12]:[c:13]:[c:14](-[C;D1;H3:15]):[c;H0;D3;+0:8]2:[c;H0;D3;+0:9]:1-[O;H0;D2;+0:4]-[C:2](=[O;D1;H0:3])-[CH;D3;+0:1]-2-[c:5](:[c:6]):[c:7] | 20 | [{"value": 20.0, "product": "C(C)(C)C1=CC=C(C=C1)C1C(OC2=C1C(=CC=C2C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using hydroxy(4-isopropylphenyl)acetic acid and 2,5-dimethylphenol synthesized in Reference Example 1, the title compound was synthesized in the same manner as in Reference Example 2. Yield 20%. Melting point: 107-109° C. (hexane-ethyl acetate).
Conditions: See reaction.notes.procedure_details.
Workup: synthesized in R... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary alcohol.Aromatic alcohol | Ester | c1ccccc1 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | HO- | CCCCCC.C(C)(=O)OCC | null | null | CC(C)c1ccc(C(O)C(=O)O)cc1.Cc1ccc(C)c(O)c1>CCCCCC.C(C)(=O)OCC>Cc1ccc(C)c2c1OC(=O)C2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ec4f4d89eb8d491e93ff22ed4a602206 | Cc1cc(C)c2c(c1C)OC(=O)C2c1ccc(Br)cc1>>Cc1cc(C)c(C(CO)c2ccc(Br)cc2)c(O)c1C | BrC1=CC=C(C=C1)C1C(OC2=C1C(=CC(=C2C)C)C)=O>>OCC(C1=CC=C(C=C1)Br)C1=C(C(=C(C=C1C)C)C)O | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:17]([c:19]1[CH3:20])[O:18][C:8](=[O:9])[CH:7]2[c:10]1[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([CH:7]([CH2:8][OH:9])[c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]2)[c:17]([OH:18])[c:19]1[CH3:20] | Cc1cc(C)c2c(c1C)OC(=O)C2c1ccc(Br)cc1 | Cc1cc(C)c(C(CO)c2ccc(Br)cc2)c(O)c1C | null | null | C(C)(=O)OCC.CCCCCC | Reduction | OtherReaction | da0d3c7a3eeadda28a29d228ff8f103888c428bfcfc295782d2b1143ff8ed39e | bb621eee13e64a87401761367bc299c7ba93ca9330953c6249ee208fbd91494f | c1ccc(Cc2ccccc2)cc1 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[O;H0;D2;+0:3]-[c:4](:[c:5]):[c:6]-[C:7]-1-[c:8]>>[OH;D1;+0:3]-[c:4](:[c:5]):[c:6]-[C:7](-[c:8])-[CH2;D2;+0:2]-[OH;D1;+0:1] | 93 | [{"value": 93.0, "product": "OCC(C1=CC=C(C=C1)Br)C1=C(C(=C(C=C1C)C)C)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3-(4-bromophenyl)-4,6,7-trimethyl-1-benzofuran-2(3H)-one obtained in Reference Example 229, the title compound was synthesized in the same manner as in Reference Example 8. Yield 93%. Melting point: 114-115° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in Reference... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol.Aromatic alcohol | c1ccc2c(c1)CCO2 | null | c1ccccc1.c1ccccc1 | null | C(C)(=O)OCC.CCCCCC | null | null | Cc1cc(C)c2c(c1C)OC(=O)C2c1ccc(Br)cc1>C(C)(=O)OCC.CCCCCC>Cc1cc(C)c(C(CO)c2ccc(Br)cc2)c(O)c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b779b47d889640da96c5e7668cbcfd13 | Cc1ccc(C)c2c1OC(=O)C2c1ccc(C(C)C)cc1>>Cc1ccc(C)c(C(CO)c2ccc(C(C)C)cc2)c1O | C(C)(C)C1=CC=C(C=C1)C1C(OC2=C1C(=CC=C2C)C)=O>>OCC(C1=CC=C(C=C1)C(C)C)C1=C(C(=CC=C1C)C)O | [CH3:1][c:2]1[cH:3][cH:4][c:5]([CH3:6])[c:7]2[c:20]1[O:21][C:9](=[O:10])[CH:8]2[c:11]1[cH:12][cH:13][c:14]([CH:15]([CH3:16])[CH3:17])[cH:18][cH:19]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH3:6])[c:7]([CH:8]([CH2:9][OH:10])[c:11]2[cH:12][cH:13][c:14]([CH:15]([CH3:16])[CH3:17])[cH:18][cH:19]2)[c:20]1[OH:21] | Cc1ccc(C)c2c1OC(=O)C2c1ccc(C(C)C)cc1 | Cc1ccc(C)c(C(CO)c2ccc(C(C)C)cc2)c1O | null | null | CCCCCC.C(C)(=O)OCC | Reduction | OtherReaction | da0d3c7a3eeadda28a29d228ff8f103888c428bfcfc295782d2b1143ff8ed39e | bb621eee13e64a87401761367bc299c7ba93ca9330953c6249ee208fbd91494f | c1ccc(Cc2ccccc2)cc1 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[O;H0;D2;+0:3]-[c:4](:[c:5]):[c:6]-[C:7]-1-[c:8]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[C:7](-[c:8])-[c:6]:[c:4](-[OH;D1;+0:3]):[c:5] | 88 | [{"value": 88.0, "product": "OCC(C1=CC=C(C=C1)C(C)C)C1=C(C(=CC=C1C)C)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3-(4-isopropylphenyl)-4,7-dimethyl-1-benzofuran-2(3H)-one synthesized in Reference Example 230, the title compound was synthesized in the same manner as in Reference Example 8. Yield 88%. Melting point: 88-89° C. (hexane-ethyl acetate).
Conditions: See reaction.notes.procedure_details.
Workup: synthesized in Refe... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol.Aromatic alcohol | c1ccc2c(c1)CCO2 | null | c1ccccc1.c1ccccc1 | null | CCCCCC.C(C)(=O)OCC | null | null | Cc1ccc(C)c2c1OC(=O)C2c1ccc(C(C)C)cc1>CCCCCC.C(C)(=O)OCC>Cc1ccc(C)c(C(CO)c2ccc(C(C)C)cc2)c1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0bbaca243d674e24814d9e921e14c104 | Cc1cc(C)c(C(CO)c2ccccc2)c(O)c1C>>Cc1cc(C)c2c(c1C)OCC2c1ccccc1 | OCC(C1=CC=CC=C1)C1=C(C(=C(C=C1C)C)C)O>>CC1=CC(=C(C2=C1C(CO2)C2=CC=CC=C2)C)C | O[CH2:11][CH:12]([c:6]1[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[c:8]([CH3:9])[c:7]1[OH:10])[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:7]([c:8]1[CH3:9])[O:10][CH2:11][CH:12]2[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | Cc1cc(C)c(C(CO)c2ccccc2)c(O)c1C | Cc1cc(C)c2c(c1C)OCC2c1ccccc1 | null | null | CO | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether (intramolecular) | 08fe01f624cfc4673e7c832ce270800ddccb38ff76736dab6575edf463f51b05 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(C2COc3ccccc32)cc1 | O-[CH2;D2;+0:1]-[C:2](-[c:3])-[c:4]:[c:5](-[OH;D1;+0:6]):[c:7]>>[c:3]-[C:2]1-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:5](:[c:7]):[c:4]-1 | 95 | [{"value": 95.0, "product": "CC1=CC(=C(C2=C1C(CO2)C2=CC=CC=C2)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2-(2-hydroxy-1-(phenyl)ethyl)-3,5,6-trimethylphenol obtained in Reference Example 231, the title compound was synthesized in the same manner as in Reference Example 13. Yield 95%. Melting point: 72-73° C. (methanol).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in Reference Example 231 | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | HO- | CO | null | null | Cc1cc(C)c(C(CO)c2ccccc2)c(O)c1C>CO>Cc1cc(C)c2c(c1C)OCC2c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e613e85e432848019457915fb46f4696 | Cc1cc(C)c(C(CO)c2ccc(Br)cc2)c(O)c1C>>Cc1cc(C)c2c(c1C)OCC2c1ccc(Br)cc1 | OCC(C1=CC=C(C=C1)Br)C1=C(C(=C(C=C1C)C)C)O>>BrC1=CC=C(C=C1)C1COC2=C1C(=CC(=C2C)C)C | O[CH2:11][CH:12]([c:6]1[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[c:8]([CH3:9])[c:7]1[OH:10])[c:13]1[cH:14][cH:15][c:16]([Br:17])[cH:18][cH:19]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:7]([c:8]1[CH3:9])[O:10][CH2:11][CH:12]2[c:13]1[cH:14][cH:15][c:16]([Br:17])[cH:18][cH:19]1 | Cc1cc(C)c(C(CO)c2ccc(Br)cc2)c(O)c1C | Cc1cc(C)c2c(c1C)OCC2c1ccc(Br)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether (intramolecular) | 08fe01f624cfc4673e7c832ce270800ddccb38ff76736dab6575edf463f51b05 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(C2COc3ccccc32)cc1 | O-[CH2;D2;+0:1]-[C:2](-[c:3])-[c:4]:[c:5](-[OH;D1;+0:6]):[c:7]>>[c:3]-[C:2]1-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:5](:[c:7]):[c:4]-1 | 95 | [{"value": 95.0, "product": "BrC1=CC=C(C=C1)C1COC2=C1C(=CC(=C2C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 2-(2-hydroxy-1-(4-bromophenyl)ethyl)-3,5,6-trimethylphenol obtained in Reference Example 232, the title compound was synthesized in the same manner as in Reference Example 13. Yield 95%. Melting point: 72-73° C. (methanol).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in Reference Example 23... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | HO- | CO | null | null | Cc1cc(C)c(C(CO)c2ccc(Br)cc2)c(O)c1C>CO>Cc1cc(C)c2c(c1C)OCC2c1ccc(Br)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eff7e8390eb746d88157f681a42d273b | Cc1c(C)c(C(CO)c2ccc(C(C)C)cc2)c(O)c(C)c1Br>>Cc1c(C)c2c(c(C)c1Br)OCC2c1ccc(C(C)C)cc1 | BrC=1C(=C(C(=C(C1C)C)C(CO)C1=CC=C(C=C1)C(C)C)O)C>>BrC1=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C(=C1C)C)C | O[CH2:12][CH:13]([c:5]1[c:3]([CH3:4])[c:2]([CH3:1])[c:9]([Br:10])[c:7]([CH3:8])[c:6]1[OH:11])[c:14]1[cH:15][cH:16][c:17]([CH:18]([CH3:19])[CH3:20])[cH:21][cH:22]1>>[CH3:1][c:2]1[c:3]([CH3:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[Br:10])[O:11][CH2:12][CH:13]2[c:14]1[cH:15][cH:16][c:17]([CH:18]([CH3:19])[CH3:20])[cH:21][cH:22... | Cc1c(C)c(C(CO)c2ccc(C(C)C)cc2)c(O)c(C)c1Br | Cc1c(C)c2c(c(C)c1Br)OCC2c1ccc(C(C)C)cc1 | null | null | CCCCCC.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether (intramolecular) | 08fe01f624cfc4673e7c832ce270800ddccb38ff76736dab6575edf463f51b05 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(C2COc3ccccc32)cc1 | O-[CH2;D2;+0:1]-[C:2](-[c:3])-[c:4]:[c:5](-[OH;D1;+0:6]):[c:7]>>[c:3]-[C:2]1-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:5](:[c:7]):[c:4]-1 | 57 | [{"value": 57.0, "product": "BrC1=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C(=C1C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3-bromo-6-(2-hydroxy-1-(4-isopropylphenyl)ethyl)-2,4,5-trimethylphenol synthesized in Reference Example 234, the title compound was synthesized in the same manner as in Reference Example 13. Yield 57%. Melting point: 56-57° C. (hexane-ethyl acetate).
Conditions: See reaction.notes.procedure_details.
Workup: synth... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | HO- | CCCCCC.C(C)(=O)OCC | null | null | Cc1c(C)c(C(CO)c2ccc(C(C)C)cc2)c(O)c(C)c1Br>CCCCCC.C(C)(=O)OCC>Cc1c(C)c2c(c(C)c1Br)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a528ad239edd4c00bec1b21972209049 | CN(C)C=O.Cc1cc(C)c2c(c1C)OCC2c1cccc(Br)c1>>Cc1cc(C)c2c(-c3cccc(C=O)c3)coc2c1C | CN(C)C=O.BrC=1C=C(C=CC1)C1COC2=C1C(=CC(=C2C)C)C.O.C(CCC)[Li]>>C(=O)C=1C=C(C=CC1)C1=COC2=C1C(=CC(=C2C)C)C | CN(C)[CH:13]=[O:14].Br[c:12]1[cH:11][cH:10][cH:9][c:8]([CH:7]2[c:6]3[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[c:19]([CH3:20])[c:18]3[O:17][CH2:16]2)[cH:15]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:7](-[c:8]3[cH:9][cH:10][cH:11][c:12]([CH:13]=[O:14])[cH:15]3)[cH:16][o:17][c:18]2[c:19]1[CH3:20] | CN(C)C=O.Cc1cc(C)c2c(c1C)OCC2c1cccc(Br)c1 | Cc1cc(C)c2c(-c3cccc(C=O)c3)coc2c1C | null | null | C1CCOC1 | C-C Coupling | OtherReaction | c4501430e312e25555f40df452a0f2686c696c726f412276c556ae5f2c2fef15 | 668a555c61cd2be29873b66eaf61c9e892723567814d4e2f115760b57901a41f | c1ccc(-c2coc3ccccc23)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c;H0;D3;+0:5](-[CH;D3;+0:6]2-[CH2;D2;+0:7]-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11]-2:[c:12]):[c:13]:1.C-N(-C)-[CH;D2;+0:14]=[O;D1;H0:15]>>[O;D1;H0:15]=[CH;D2;+0:14]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:6]2:[cH;D2;+0:7]:[o;H0;D2;+0:8]:[c:9](:[c:10]):[c:11]:2:[c... | null | [] | null | null | 30 | MINUTE | To a solution of 3-(3-bromophenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran obtained in Reference Example 203 (1.77 g, 5.57 mmol) in THF (20 mL) was added dropwise n-butyllithium (1.6 M hexane solution, 4.18 mL, 6.68 mmol) under argon atmosphere at −78° C., and the mixture was stirred for 30 minutes. To the reaction so... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Tertiary amide | Aldehyde | c1ccccc1.c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2occc2c1 | c1ccccc1.c1ccc2occc2c1 | HBr | C1CCOC1 | null | 0.5 | CN(C)C=O.Cc1cc(C)c2c(c1C)OCC2c1cccc(Br)c1>C1CCOC1>Cc1cc(C)c2c(-c3cccc(C=O)c3)coc2c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a3e3b849c26f43609d0310194812dc16 | CO.Cc1cc(C)c2c(c1C)OCC2c1ccc(Br)cc1>>Cc1cc(C)c2c(c1C)OCC2c1ccc(C=O)cc1 | BrC1=CC=C(C=C1)C1COC2=C1C(=CC(=C2C)C)C.CO>>C(=O)C1=CC=C(C=C1)C1COC2=C1C(=CC(=C2C)C)C | [CH3:17][OH:18].Br[c:16]1[cH:15][cH:14][c:13]([CH:12]2[c:6]3[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[c:8]([CH3:9])[c:7]3[O:10][CH2:11]2)[cH:20][cH:19]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:7]([c:8]1[CH3:9])[O:10][CH2:11][CH:12]2[c:13]1[cH:14][cH:15][c:16]([CH:17]=[O:18])[cH:19][cH:20]1 | CO.Cc1cc(C)c2c(c1C)OCC2c1ccc(Br)cc1 | Cc1cc(C)c2c(c1C)OCC2c1ccc(C=O)cc1 | null | null | null | Acylation | OtherReaction | 2778df8f9aafa33c27325b5f551fb7988cb9555417961c82601465bea5169117 | 9eaf52e1d6c807379caf76f387686adf715a7c3d144d198ad175de799903bae9 | c1ccc(C2COc3ccccc32)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[CH3;D1;+0:6]-[OH;D1;+0:7]>>[O;H0;D1;+0:7]=[CH;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 73 | [{"value": 73.0, "product": "C(=O)C1=CC=C(C=C1)C1COC2=C1C(=CC(=C2C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3-(4-bromophenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran obtained in Reference Example 236, the title compound was synthesized in the same manner as in Reference Example 245. Yield 73%. Melting point: 87-88° C. (methanol).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in Reference Example 2... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Methanol | Aldehyde | c1ccccc1 | c1ccccc1 | c1ccc2c(c1)CCO2.c1ccccc1 | HBr | null | null | null | CO.Cc1cc(C)c2c(c1C)OCC2c1ccc(Br)cc1>>Cc1cc(C)c2c(c1C)OCC2c1ccc(C=O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f6774376290a4ed38a2b5fbe100167ef | Cc1c2c(c3ccccc3c1O)OCC2c1ccc(C(C)C)cc1.O=S(=O)([O-])C(F)(F)F>>Cc1c2c(c3ccccc3c1OS(=O)(=O)C(F)(F)F)OCC2c1ccc(C(C)C)cc1 | O.C(C)(C)C1=CC=C(C=C1)C1C2=C(OC1)C1=CC=CC=C1C(=C2C)O.FC(S(=O)(=O)[O-])(F)F>>FC(S(=O)(=O)OC1=C(C2=C(OCC2C2=CC=C(C=C2)C(C)C)C2=CC=CC=C12)C)(F)F | [CH3:1][c:2]1[c:3]2[c:4]([c:5]3[cH:6][cH:7][cH:8][cH:9][c:10]3[c:11]1[OH:12])[O:20][CH2:21][CH:22]2[c:23]1[cH:24][cH:25][c:26]([CH:27]([CH3:28])[CH3:29])[cH:30][cH:31]1.[O-][S:13](=[O:14])(=[O:15])[C:16]([F:17])([F:18])[F:19]>>[CH3:1][c:2]1[c:3]2[c:4]([c:5]3[cH:6][cH:7][cH:8][cH:9][c:10]3[c:11]1[O:12][S:13](=[O:14])(=[... | Cc1c2c(c3ccccc3c1O)OCC2c1ccc(C(C)C)cc1.O=S(=O)([O-])C(F)(F)F | Cc1c2c(c3ccccc3c1OS(=O)(=O)C(F)(F)F)OCC2c1ccc(C(C)C)cc1 | null | CN(C1=CC=NC=C1)C | N1=CC=CC=C1 | Miscellaneous | OtherReaction | ba84d08741dc57cca837179da107c727f33f41827c881049a0cab23247fbb369 | fcecc986e6b6ef358a6dd65b54f52d1bac6e13854a99d0d8523194ad4b1de7ad | c1ccc(C2COc3c2ccc2ccccc32)cc1 | [F;D1;H0:1]-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[S;H0;D4;+0:5](-[O-])(=[O;D1;H0:6])=[O;D1;H0:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[F;D1;H0:1]-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[S;H0;D4;+0:5](=[O;D1;H0:6])(=[O;D1;H0:7])-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11] | 76 | [{"value": 76.0, "product": "FC(S(=O)(=O)OC1=C(C2=C(OCC2C2=CC=C(C=C2)C(C)C)C2=CC=CC=C12)C)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 8 | HOUR | To a solution of 3-(4-isopropylphenyl)-4-methyl-2,3-dihydronaphtho[1,2-b]furan-5-ol obtained in Reference Example 252 (2.60 g, 8.17 mmol) and 4-dimethylaminopyridine (2.0 g, 16.3 mmol) in pyridine (30 mL) was added anhydrous trifluoromethanesulfonate (1.51 mL, 9.00 mmol) at room temperature at 0° C., and the mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Sulfonic acid | Triflate | null | null | c1ccc2c3c(ccc2c1)CCO3.c1ccccc1 | HO- | CN(C1=CC=NC=C1)C.N1=CC=CC=C1 | 50 | 8 | Cc1c2c(c3ccccc3c1O)OCC2c1ccc(C(C)C)cc1.O=S(=O)([O-])C(F)(F)F>CN(C1=CC=NC=C1)C.N1=CC=CC=C1>Cc1c2c(c3ccccc3c1OS(=O)(=O)C(F)(F)F)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a3d7a114b29641cb92f498cf4b8898b9 | Cc1c2c(c3ccccc3c1OS(=O)(=O)C(F)(F)F)OCC2c1ccc(C(C)C)cc1>>Cc1cc2ccccc2c2c1C(c1ccc(C(C)C)cc1)CO2 | FC(S(=O)(=O)OC1=C(C2=C(OCC2C2=CC=C(C=C2)C(C)C)C2=CC=CC=C12)C)(F)F.C(=O)O.C1(=CC=CC=C1)P(CCCP(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.C(CCC)N(CCCC)CCCC>>C(C)(C)C1=CC=C(C=C1)C1C2=C(OC1)C1=CC=CC=C1C=C2C | O=S(=O)(O[c:3]1[c:2]([CH3:1])[c:11]2[c:10]([c:9]3[c:4]1[cH:5][cH:6][cH:7][cH:8]3)[O:23][CH2:22][CH:12]2[c:13]1[cH:14][cH:15][c:16]([CH:17]([CH3:18])[CH3:19])[cH:20][cH:21]1)C(F)(F)F>>[CH3:1][c:2]1[cH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[c:10]2[c:11]1[CH:12]([c:13]1[cH:14][cH:15][c:16]([CH:17]([CH3:18])[CH3:19])[cH:20... | Cc1c2c(c3ccccc3c1OS(=O)(=O)C(F)(F)F)OCC2c1ccc(C(C)C)cc1 | Cc1cc2ccccc2c2c1C(c1ccc(C(C)C)cc1)CO2 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | O.C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | fde61a66a3491048763557d341ce960743558cfa6f076ee6f86ee5524b258387 | b176f4ca0adee4f5ff077805596a10ddc6aa820843e17b6a0f5ce62bb8d509d7 | c1ccc(C2COc3c2ccc2ccccc32)cc1 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1](:[c:2](-[C;D1;H3:3]):[c:4]):[c:5](:[c:6]):[c:7]>>[C;D1;H3:3]-[c:2](:[c:4]):[cH;D2;+0:1]:[c:5](:[c:6]):[c:7] | 18 | [{"value": 18.0, "product": "C(C)(C)C1=CC=C(C=C1)C1C2=C(OC1)C1=CC=CC=C1C=C2C", "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 16 | HOUR | To a solution of 3-(4-isopropylphenyl)-4-methyl-2,3-dihydronaphtho[1,2-b]furan-5-yl trifluoromethanesulfonate obtained in Reference Example 253 (2.23 g, 4.96 mmol), dichlorobis(triphenylphosphine)palladium (210 mg, 0.30 mmol), 1,3-bis(diphenylphosphino)propane (310 mg, 0.750 mmol) and tributylamine (5 mL, 21 mmol) in t... | 10.6084/m9.figshare.5104873.v1 | null | Triflate | null | c1ccc2c3c(ccc2c1)CCO3 | c1ccc2c3c(ccc2c1)CCO3 | c1ccccc1.c1ccc2c3c(ccc2c1)CCO3 | TfOH | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.O.C1(=CC=CC=C1)C | 90 | 16 | Cc1c2c(c3ccccc3c1OS(=O)(=O)C(F)(F)F)OCC2c1ccc(C(C)C)cc1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.O.C1(=CC=CC=C1)C>Cc1cc2ccccc2c2c1C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dd1d582100874cf2a700319f4d172666 | Cc1cc(C)c(C)c(OCC(=O)O)c1>>Cc1cc(C)c2c(c1C)OCC2=O | CC1=C(OCC(=O)O)C=C(C=C1C)C>>CC1=CC(=C(C2=C1C(CO2)=O)C)C | O[C:12]([CH2:11][O:10][c:7]1[cH:6][c:4]([CH3:5])[cH:3][c:2]([CH3:1])[c:8]1[CH3:9])=[O:13]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:7]([c:8]1[CH3:9])[O:10][CH2:11][C:12]2=[O:13] | Cc1cc(C)c(C)c(OCC(=O)O)c1 | Cc1cc(C)c2c(c1C)OCC2=O | null | null | CCCCCC | Functional Group Interconversion | OtherReaction | 07c0617fba4b5b8b4f6e211c6b50ebf5bf60539aad6b1d235a93c13cf5d42336 | 6a71bb5a71b59feeb4f6a39b1b66fa450a058b64b0a3909e1a51c22473a141c5 | O=C1COc2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8](-[C;D1;H3:9]):[c:10]>>[C;D1;H3:9]-[c:8](:[c:10]):[c;H0;D3;+0:7]1:[c:5](:[c:6])-[#8:4]-[C:3]-[C;H0;D3;+0:1]-1=[O;D1;H0:2] | 75 | [{"value": 75.0, "product": "CC1=CC(=C(C2=C1C(CO2)=O)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using (2,3,5-trimethylphenoxy)acetic acid obtained in Reference Example 158, the title compound was synthesized in the same manner as in Reference Example 41. Yield 75%. Melting point: 92-93° C. (hexane).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in Reference Example 158 | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | c1ccccc1 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | HO- | CCCCCC | null | null | Cc1cc(C)c(C)c(OCC(=O)O)c1>CCCCCC>Cc1cc(C)c2c(c1C)OCC2=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e41f759fb0f443a087884c5e0daabf11 | CCc1ccc(B(O)O)cc1.Cc1c(Br)c(C)c2c(OS(=O)(=O)C(F)(F)F)coc2c1C>>CCc1ccc(-c2coc3c(C)c(C)c(Br)c(C)c23)cc1 | FC(S(=O)(=O)OC1=COC2=C1C(=C(C(=C2C)C)Br)C)(F)F.C(C)O.C(C)C1=CC=C(C=C1)B(O)O.C([O-])([O-])=O.[Na+].[Na+]>>BrC=1C(=C(C2=C(C(=CO2)C2=CC=C(C=C2)CC)C1C)C)C | OB(O)[c:6]1[cH:5][cH:4][c:3]([CH2:2][CH3:1])[cH:21][cH:20]1.O=S(=O)(O[c:7]1[cH:8][o:9][c:10]2[c:11]([CH3:12])[c:13]([CH3:14])[c:15]([Br:16])[c:17]([CH3:18])[c:19]12)C(F)(F)F>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][o:9][c:10]3[c:11]([CH3:12])[c:13]([CH3:14])[c:15]([Br:16])[c:17]([CH3:18])[c:19]23)[cH:20][cH... | CCc1ccc(B(O)O)cc1.Cc1c(Br)c(C)c2c(OS(=O)(=O)C(F)(F)F)coc2c1C | CCc1ccc(-c2coc3c(C)c(C)c(Br)c(C)c23)cc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O.C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids OTf | f75d3a560a4330e839583381be3b65b24b6b7bd0db86a3a67cb12bc3661f7953 | 3f602cf53fbcf2a56d992979503f6bea55727095a6b9075475a711784170b440 | c1ccc(-c2coc3ccccc23)cc1 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1]1:[c:2]:[#8;a:3]:[c:4](:[c:5]):[c:6]:1:[c:7].O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[c:5]:[c:4]1:[#8;a:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:6]:1:[c:7] | 92 | [{"value": 92.0, "product": "BrC=1C(=C(C2=C(C(=CO2)C2=CC=C(C=C2)CC)C1C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixed solution of 5-bromo-4,6,7-trimethyl-1-benzofuran-3-yl trifluoromethanesulfonate obtained in Reference Example 261 (1.35 g, 3.49 mmol), 4-ethylphenyl boronic acid (523 mg, 3.49 mmol), tetrakis(triphenylphosphine)palladium(0) (81 mg, 0.07 mmol) in a 2 N aqueous sodium carbonate solution (4 mL)-ethanol (4 mL)-tolu... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Boronic acid | null | c1ccccc1.c1ccc2occc2c1 | c1ccccc1.c1ccc2occc2c1 | c1ccccc1.c1ccc2occc2c1 | TfOH.HO-.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C1(=CC=CC=C1)C | null | null | CCc1ccc(B(O)O)cc1.Cc1c(Br)c(C)c2c(OS(=O)(=O)C(F)(F)F)coc2c1C>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C1(=CC=CC=C1)C>CCc1ccc(-c2coc3c(C)c(C)c(Br)c(C)c23)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-81d75eec7bbf4269b79ba5de21a54f97 | Cc1cc(C)c(Cc2ccc(C(C)C)cc2)c(OC(C)(C)C(=O)O)c1>>Cc1cc(C)c2c(c1Cc1ccc(C(C)C)cc1)OC(C)(C)C2=O | [Cl-].[Al+3].[Cl-].[Cl-].C(C)(C)C1=CC=C(CC2=C(OC(C(=O)O)(C)C)C=C(C=C2C)C)C=C1.C(C(=O)Cl)(=O)Cl>>C(C)(C)C1=CC=C(CC2=C(C=C(C=3C(C(OC32)(C)C)=O)C)C)C=C1 | O[C:23]([C:20]([O:19][c:7]1[c:6]([CH2:9][c:10]2[cH:11][cH:12][c:13]([CH:14]([CH3:15])[CH3:16])[cH:17][cH:18]2)[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:8]1)([CH3:21])[CH3:22])=[O:24]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:7]([c:8]1[CH2:9][c:10]1[cH:11][cH:12][c:13]([CH:14]([CH3:15])[CH3:16])[cH:17][cH:18]1)[O:19][C:20]... | Cc1cc(C)c(Cc2ccc(C(C)C)cc2)c(OC(C)(C)C(=O)O)c1 | Cc1cc(C)c2c(c1Cc1ccc(C(C)C)cc1)OC(C)(C)C2=O | null | CN(C)C=O | ClCCl.C1CCOC1 | Functional Group Interconversion | OtherReaction | 07c0617fba4b5b8b4f6e211c6b50ebf5bf60539aad6b1d235a93c13cf5d42336 | 6a71bb5a71b59feeb4f6a39b1b66fa450a058b64b0a3909e1a51c22473a141c5 | O=C1COc2c(Cc3ccccc3)cccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[#8:6]-[c:7]1:[cH;D2;+0:8]:[c:9](-[C;D1;H3:10]):[c:11]:[c:12](-[C;D1;H3:13]):[c;H0;D3;+0:14]:1-[CH2;D2;+0:15]-[c:16](:[c:17]):[c:18]>>[C;D1;H3:10]-[c:9]1:[c:11]:[c:12](-[C;D1;H3:13]):[c;H0;D3;+0:14]2:[c:7](:[c;H0;D3;+0:8]:1-[CH2;D2;+0:15]-[c:16](:[c:17]):... | 64 | [{"value": 64.0, "product": "C(C)(C)C1=CC=C(CC2=C(C=C(C=3C(C(OC32)(C)C)=O)C)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To a solution of 2-(2-(4-isopropylbenzyl)-3,5-dimethylphenoxy)-2-methylpropanoic acid obtained in Reference Example 156 (5.55 g, 16.3 mmol) in THF (50 mL) was added dropwise oxalyl chloride (2.13 mL, 24.5 mmol) with ice-cooling. The mixture was stirred for 20 minutes, and DMF (3 drops) was added thereto, and the mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | c1ccccc1 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | HO- | CN(C)C=O.ClCCl.C1CCOC1 | null | 0.333333 | Cc1cc(C)c(Cc2ccc(C(C)C)cc2)c(OC(C)(C)C(=O)O)c1>CN(C)C=O.ClCCl.C1CCOC1>Cc1cc(C)c2c(c1Cc1ccc(C(C)C)cc1)OC(C)(C)C2=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3219bdee6e9749aa83f465b79f66172e | Cc1cc2c(c(C)c1Br)C(c1ccc(C(C)C)cc1)CS2.N=C(c1ccccc1)c1ccccc1>>Cc1cc2c(c(C)c1N=C(c1ccccc1)c1ccccc1)C(c1ccc(C(C)C)cc1)CS2 | C=1C=CC(=CC1)P(C=2C=CC=CC2)C3=CC=C4C=CC=CC4=C3C5=C6C=CC=CC6=CC=C5P(C=7C=CC=CC7)C=8C=CC=CC8.BrC=1C(=CC2=C(C(CS2)C2=CC=C(C=C2)C(C)C)C1C)C.CC(C)([O-])C.[Na+].C(C1=CC=CC=C1)(C1=CC=CC=C1)=N>>C1(=CC=CC=C1)C(=NC=1C(=CC2=C(C(CS2)C2=CC=C(C=C2)C(C)C)C1C)C)C1=CC=CC=C1 | Br[c:8]1[c:2]([CH3:1])[cH:3][c:4]2[c:5]([c:6]1[CH3:7])[CH:23]([c:24]1[cH:25][cH:26][c:27]([CH:28]([CH3:29])[CH3:30])[cH:31][cH:32]1)[CH2:33][S:34]2.[NH:9]=[C:10]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([c:6]([CH3:7])[c:8]1[N:9]=[C:10]([c:11... | Cc1cc2c(c(C)c1Br)C(c1ccc(C(C)C)cc1)CS2.N=C(c1ccccc1)c1ccccc1 | Cc1cc2c(c(C)c1N=C(c1ccccc1)c1ccccc1)C(c1ccc(C(C)C)cc1)CS2 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | O.C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 15c364875fd47fe314d1f0f4daf94b29dadb39b96c4331dabf8d9409fba372d1 | d6fdf3485f414343350878d3990b407f7838ca1f9344576c0f428d9ed6db7945 | c1ccc(C(=Nc2ccc3c(c2)C(c2ccccc2)CS3)c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2](-[C;D1;H3:3]):[c:4]):[c:5](-[C;D1;H3:6]):[c:7].[NH;D1;+0:8]=[C:9](-[c:10])-[c:11]>>[C;D1;H3:3]-[c:2](:[c:4]):[c;H0;D3;+0:1](-[N;H0;D2;+0:8]=[C:9](-[c:10])-[c:11]):[c:5](-[C;D1;H3:6]):[c:7] | null | [] | null | null | 15 | MINUTE | To a solution of 5-bromo-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzothiophene obtained in Reference Example 259 (870 mg, 2.41 mmol) and benzophenone imine (0.76 mL, 2.89 mmol) in toluene (15 mL) were added tris(dibenzylideneacetone)dipalladium (22 mg, 0.024 mmol) and BINAP (45 mg, 0.072 mmol) at room tempera... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Unsubstituted imine | Substituted imine | c1ccc2c(c1)CCS2 | c1ccc2c(c1)CCS2 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2c(c1)CCS2 | HBr | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O.C1(=CC=CC=C1)C | null | 0.25 | Cc1cc2c(c(C)c1Br)C(c1ccc(C(C)C)cc1)CS2.N=C(c1ccccc1)c1ccccc1>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O.C1(=CC=CC=C1)C>Cc1cc2c(c(C)c1N=C(c1ccccc1)c1ccccc1)C(c1ccc(C(C)C)cc1)CS2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-24581ef9259c4d128f23470605c4bdc2 | Cc1cc2c(c(C)c1NCc1ccccc1)CCO2>>Cc1cc2c(c(C)c1N)CCO2 | C(C1=CC=CC=C1)NC=1C(=CC2=C(CCO2)C1C)C>>CC1=C(C(=CC2=C1CCO2)C)N | c1ccc(C[NH:9][c:8]2[c:2]([CH3:1])[cH:3][c:4]3[c:5]([c:6]2[CH3:7])[CH2:10][CH2:11][O:12]3)cc1>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([c:6]([CH3:7])[c:8]1[NH2:9])[CH2:10][CH2:11][O:12]2 | Cc1cc2c(c(C)c1NCc1ccccc1)CCO2 | Cc1cc2c(c(C)c1N)CCO2 | null | null | C(C)(=O)OCC.CCCCCC | Deprotection | OtherReaction | 93c46c2f9981b731115295839d7158a8a73faedd00707b7604ace2fa5f580cbc | f6571fb5b7780a2b467937abfba91ba7d787f19d503265f299ff4a25a08963bd | c1ccc2c(c1)CCO2 | [c:1]:[c:2](-[NH;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[NH2;D1;+0:3]-[c:2](:[c:1]):[c:4] | 86 | [{"value": 86.0, "product": "CC1=C(C(=CC2=C1CCO2)C)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-benzyl-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-amine obtained in Reference Example 270, the title compound was synthesized in the same manner as in Reference Example 30. Yield 86%. Melting point: 85-86° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in Reference Ex... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | c1ccccc1 | null | c1ccc2c(c1)CCO2 | Other | C(C)(=O)OCC.CCCCCC | null | null | Cc1cc2c(c(C)c1NCc1ccccc1)CCO2>C(C)(=O)OCC.CCCCCC>Cc1cc2c(c(C)c1N)CCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-298630fe7309428287c3f2bda68e20da | Cc1c2c(c(Cc3ccc(C(C)C)cc3)c(C)c1NCc1ccccc1)OCC2>>Cc1c(N)c(C)c(Cc2ccc(C(C)C)cc2)c2c1CCO2 | C(C1=CC=CC=C1)NC=1C(=C(C2=C(CCO2)C1C)CC1=CC=C(C=C1)C(C)C)C>>C(C)(C)C1=CC=C(CC2=C(C(=C(C=3CCOC32)C)N)C)C=C1 | c1ccc(C[NH:4][c:3]2[c:2]([CH3:1])[c:19]3[c:18]([c:7]([CH2:8][c:9]4[cH:10][cH:11][c:12]([CH:13]([CH3:14])[CH3:15])[cH:16][cH:17]4)[c:5]2[CH3:6])[O:22][CH2:21][CH2:20]3)cc1>>[CH3:1][c:2]1[c:3]([NH2:4])[c:5]([CH3:6])[c:7]([CH2:8][c:9]2[cH:10][cH:11][c:12]([CH:13]([CH3:14])[CH3:15])[cH:16][cH:17]2)[c:18]2[c:19]1[CH2:20][CH... | Cc1c2c(c(Cc3ccc(C(C)C)cc3)c(C)c1NCc1ccccc1)OCC2 | Cc1c(N)c(C)c(Cc2ccc(C(C)C)cc2)c2c1CCO2 | null | null | C(C)(=O)OCC.CCCCCC | Deprotection | OtherReaction | 93c46c2f9981b731115295839d7158a8a73faedd00707b7604ace2fa5f580cbc | f6571fb5b7780a2b467937abfba91ba7d787f19d503265f299ff4a25a08963bd | c1ccc(Cc2cccc3c2OCC3)cc1 | [c:1]:[c:2](-[NH;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[NH2;D1;+0:3]-[c:2](:[c:1]):[c:4] | 92 | [{"value": 92.0, "product": "C(C)(C)C1=CC=C(CC2=C(C(=C(C=3CCOC32)C)N)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-benzyl-7-(4-isopropylbenzyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-amine obtained in Reference Example 271, the title compound was synthesized in the same manner as in Reference Example 30. Yield 92%. Melting point: 114-115° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details.
Workup: ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)CCO2 | Other | C(C)(=O)OCC.CCCCCC | null | null | Cc1c2c(c(Cc3ccc(C(C)C)cc3)c(C)c1NCc1ccccc1)OCC2>C(C)(=O)OCC.CCCCCC>Cc1c(N)c(C)c(Cc2ccc(C(C)C)cc2)c2c1CCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-03335b1f1f874c46a44bae04bf2e5529 | COc1cc(C)c(NCc2ccccc2)c(C)c1Cc1ccc(C(C)C)cc1>>COc1cc(C)c(N)c(C)c1Cc1ccc(C(C)C)cc1 | C(C1=CC=CC=C1)NC1=C(C(=C(C=C1C)OC)CC1=CC=C(C=C1)C(C)C)C>>C(C)(C)C1=CC=C(CC=2C(=C(C(=CC2OC)C)N)C)C=C1 | c1ccc(C[NH:8][c:7]2[c:5]([CH3:6])[cH:4][c:3]([O:2][CH3:1])[c:11]([CH2:12][c:13]3[cH:14][cH:15][c:16]([CH:17]([CH3:18])[CH3:19])[cH:20][cH:21]3)[c:9]2[CH3:10])cc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[c:7]([NH2:8])[c:9]([CH3:10])[c:11]1[CH2:12][c:13]1[cH:14][cH:15][c:16]([CH:17]([CH3:18])[CH3:19])[cH:20][cH:21]1 | COc1cc(C)c(NCc2ccccc2)c(C)c1Cc1ccc(C(C)C)cc1 | COc1cc(C)c(N)c(C)c1Cc1ccc(C(C)C)cc1 | null | null | C(C)(=O)OCC.CCCCCC | Deprotection | OtherReaction | 93c46c2f9981b731115295839d7158a8a73faedd00707b7604ace2fa5f580cbc | f6571fb5b7780a2b467937abfba91ba7d787f19d503265f299ff4a25a08963bd | c1ccc(Cc2ccccc2)cc1 | [c:1]:[c:2](-[NH;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[NH2;D1;+0:3]-[c:2](:[c:1]):[c:4] | 86 | [{"value": 86.0, "product": "C(C)(C)C1=CC=C(CC=2C(=C(C(=CC2OC)C)N)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-benzyl-3-(4-isopropylbenzyl)-4-methoxy-2,6-dimethylaniline obtained in Reference Example 267, the title compound was synthesized in the same manner as in Reference Example 30. Yield 86%. Melting point: 91-92° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in Refere... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | c1ccccc1 | null | c1ccccc1.c1ccccc1 | Other | C(C)(=O)OCC.CCCCCC | null | null | COc1cc(C)c(NCc2ccccc2)c(C)c1Cc1ccc(C(C)C)cc1>C(C)(=O)OCC.CCCCCC>COc1cc(C)c(N)c(C)c1Cc1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d6776d5688fa4033885ddbf3bbcbd3c2 | COc1cc(C(C)C)ccc1C1COc2c(C)c(C)c(NCc3ccccc3)c(C)c21>>COc1cc(C(C)C)ccc1C1COc2c(C)c(C)c(N)c(C)c21 | C(C1=CC=CC=C1)NC=1C(=C(C2=C(C(CO2)C2=C(C=C(C=C2)C(C)C)OC)C1C)C)C>>C(C)(C)C1=CC(=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)N)C)OC | c1ccc(C[NH:21][c:20]2[c:18]([CH3:19])[c:16]([CH3:17])[c:15]3[c:24]([c:22]2[CH3:23])[CH:12]([c:11]2[c:3]([O:2][CH3:1])[cH:4][c:5]([CH:6]([CH3:7])[CH3:8])[cH:9][cH:10]2)[CH2:13][O:14]3)cc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]([CH3:7])[CH3:8])[cH:9][cH:10][c:11]1[CH:12]1[CH2:13][O:14][c:15]2[c:16]([CH3:17])[c:18]([CH3:19... | COc1cc(C(C)C)ccc1C1COc2c(C)c(C)c(NCc3ccccc3)c(C)c21 | COc1cc(C(C)C)ccc1C1COc2c(C)c(C)c(N)c(C)c21 | null | null | C(C)(=O)OCC.CCCCCC | Deprotection | OtherReaction | 93c46c2f9981b731115295839d7158a8a73faedd00707b7604ace2fa5f580cbc | f6571fb5b7780a2b467937abfba91ba7d787f19d503265f299ff4a25a08963bd | c1ccc(C2COc3ccccc32)cc1 | [c:1]:[c:2](-[NH;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[NH2;D1;+0:3]-[c:2](:[c:1]):[c:4] | 87 | [{"value": 87.0, "product": "C(C)(C)C1=CC(=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)N)C)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-benzyl-3-(4-isopropyl-2-methoxyphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-amine obtained in Reference Example 273, the title compound was synthesized in the same manner as in Reference Example 30. Yield 87%. Melting point: 120-121° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_deta... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)CCO2 | Other | C(C)(=O)OCC.CCCCCC | null | null | COc1cc(C(C)C)ccc1C1COc2c(C)c(C)c(NCc3ccccc3)c(C)c21>C(C)(=O)OCC.CCCCCC>COc1cc(C(C)C)ccc1C1COc2c(C)c(C)c(N)c(C)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a28f461210474d8f98efbc01cab877db | Cc1c(C)c2c(c(C)c1NCc1ccccc1)C(c1ccccc1)CO2>>Cc1c(C)c2c(c(C)c1N)C(c1ccccc1)CO2 | C(C1=CC=CC=C1)NC=1C(=C(C2=C(C(CO2)C2=CC=CC=C2)C1C)C)C>>CC1=C(C(=C(C2=C1C(CO2)C2=CC=CC=C2)C)C)N | c1ccc(C[NH:10][c:9]2[c:2]([CH3:1])[c:3]([CH3:4])[c:5]3[c:6]([c:7]2[CH3:8])[CH:11]([c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[CH2:18][O:19]3)cc1>>[CH3:1][c:2]1[c:3]([CH3:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH2:10])[CH:11]([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[CH2:18][O:19]2 | Cc1c(C)c2c(c(C)c1NCc1ccccc1)C(c1ccccc1)CO2 | Cc1c(C)c2c(c(C)c1N)C(c1ccccc1)CO2 | null | null | C(C)(=O)OCC.CCCCCC | Deprotection | OtherReaction | 93c46c2f9981b731115295839d7158a8a73faedd00707b7604ace2fa5f580cbc | f6571fb5b7780a2b467937abfba91ba7d787f19d503265f299ff4a25a08963bd | c1ccc(C2COc3ccccc32)cc1 | [c:1]:[c:2](-[NH;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[NH2;D1;+0:3]-[c:2](:[c:1]):[c:4] | 72 | [{"value": 72.0, "product": "CC1=C(C(=C(C2=C1C(CO2)C2=CC=CC=C2)C)C)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-benzyl-4,6,7-trimethyl-3-phenyl-2,3-dihydro-1-benzofuran-5-amine obtained in Reference Example 276, the title compound was synthesized in the same manner as in Reference Example 30. Yield 72%. Melting point: 94-95° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)CCO2 | Other | C(C)(=O)OCC.CCCCCC | null | null | Cc1c(C)c2c(c(C)c1NCc1ccccc1)C(c1ccccc1)CO2>C(C)(=O)OCC.CCCCCC>Cc1c(C)c2c(c(C)c1N)C(c1ccccc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5b3c0fb5a292498aaca3c6147fee1e5f | Cc1ccc(C2COc3c(C)c(C)c(NCc4ccccc4)c(C)c32)cc1>>Cc1ccc(C2COc3c(C)c(C)c(N)c(C)c32)cc1 | C(C1=CC=CC=C1)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C)C1C)C)C>>CC1=C(C(=C(C2=C1C(CO2)C2=CC=C(C=C2)C)C)C)N | c1ccc(C[NH:15][c:14]2[c:12]([CH3:13])[c:10]([CH3:11])[c:9]3[c:18]([c:16]2[CH3:17])[CH:6]([c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:20][cH:19]2)[CH2:7][O:8]3)cc1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]2[CH2:7][O:8][c:9]3[c:10]([CH3:11])[c:12]([CH3:13])[c:14]([NH2:15])[c:16]([CH3:17])[c:18]32)[cH:19][cH:20]1 | Cc1ccc(C2COc3c(C)c(C)c(NCc4ccccc4)c(C)c32)cc1 | Cc1ccc(C2COc3c(C)c(C)c(N)c(C)c32)cc1 | null | null | CCCCCC | Deprotection | OtherReaction | 93c46c2f9981b731115295839d7158a8a73faedd00707b7604ace2fa5f580cbc | f6571fb5b7780a2b467937abfba91ba7d787f19d503265f299ff4a25a08963bd | c1ccc(C2COc3ccccc32)cc1 | [c:1]:[c:2](-[NH;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[NH2;D1;+0:3]-[c:2](:[c:1]):[c:4] | 91 | [{"value": 91.0, "product": "CC1=C(C(=C(C2=C1C(CO2)C2=CC=C(C=C2)C)C)C)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-benzyl-4,6,7-trimethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-amine obtained in Reference Example 277, the title compound was synthesized in the same manner as in Reference Example 30. Yield 91%. Melting point: 121-122° C. (hexane).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in Re... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)CCO2 | Other | CCCCCC | null | null | Cc1ccc(C2COc3c(C)c(C)c(NCc4ccccc4)c(C)c32)cc1>CCCCCC>Cc1ccc(C2COc3c(C)c(C)c(N)c(C)c32)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-24d71f05c78340c59690840fb8f35f68 | Cc1ccc(C2COc3c(C)c(C)c(NCc4ccccc4)c(C)c32)nc1>>Cc1ccc(C2COc3c(C)c(C)c(N)c(C)c32)nc1 | C(C1=CC=CC=C1)NC=1C(=C(C2=C(C(CO2)C2=NC=C(C=C2)C)C1C)C)C>>CC1=C(C(=C(C2=C1C(CO2)C2=NC=C(C=C2)C)C)C)N | c1ccc(C[NH:15][c:14]2[c:12]([CH3:13])[c:10]([CH3:11])[c:9]3[c:18]([c:16]2[CH3:17])[CH:6]([c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:20][n:19]2)[CH2:7][O:8]3)cc1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]2[CH2:7][O:8][c:9]3[c:10]([CH3:11])[c:12]([CH3:13])[c:14]([NH2:15])[c:16]([CH3:17])[c:18]32)[n:19][cH:20]1 | Cc1ccc(C2COc3c(C)c(C)c(NCc4ccccc4)c(C)c32)nc1 | Cc1ccc(C2COc3c(C)c(C)c(N)c(C)c32)nc1 | null | null | C(C)(=O)OCC.CCCCCC | Deprotection | OtherReaction | 93c46c2f9981b731115295839d7158a8a73faedd00707b7604ace2fa5f580cbc | f6571fb5b7780a2b467937abfba91ba7d787f19d503265f299ff4a25a08963bd | c1ccc(C2COc3ccccc32)nc1 | [c:1]:[c:2](-[NH;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[NH2;D1;+0:3]-[c:2](:[c:1]):[c:4] | 85 | [{"value": 85.0, "product": "CC1=C(C(=C(C2=C1C(CO2)C2=NC=C(C=C2)C)C)C)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-benzyl-4,6,7-trimethyl-3-(5-methylpyridin-2-yl)-2,3-dihydro-1-benzofuran-5-amine obtained in Reference Example 278, the title compound was synthesized in the same manner as in Reference Example 30. Yield 85%. Melting point: 125-127° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details.
Wo... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | c1ccccc1 | null | c1ccncc1.c1ccc2c(c1)CCO2 | Other | C(C)(=O)OCC.CCCCCC | null | null | Cc1ccc(C2COc3c(C)c(C)c(NCc4ccccc4)c(C)c32)nc1>C(C)(=O)OCC.CCCCCC>Cc1ccc(C2COc3c(C)c(C)c(N)c(C)c32)nc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-db6b6d5027a0425e9f381310d46aa1b5 | Cc1c(C)c2c(c(C)c1NCc1ccccc1)C(c1ccc(-c3ccccc3)cc1)CO2>>Cc1c(C)c2c(c(C)c1N)C(c1ccc(-c3ccccc3)cc1)CO2 | C(C1=CC=CC=C1)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C2=CC=CC=C2)C1C)C)C>>C1(=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)N)C)C2=CC=CC=C2 | c1ccc(C[NH:10][c:9]2[c:2]([CH3:1])[c:3]([CH3:4])[c:5]3[c:6]([c:7]2[CH3:8])[CH:11]([c:12]2[cH:13][cH:14][c:15](-[c:16]4[cH:17][cH:18][cH:19][cH:20][cH:21]4)[cH:22][cH:23]2)[CH2:24][O:25]3)cc1>>[CH3:1][c:2]1[c:3]([CH3:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH2:10])[CH:11]([c:12]1[cH:13][cH:14][c:15](-[c:16]3[cH:17][cH:18][c... | Cc1c(C)c2c(c(C)c1NCc1ccccc1)C(c1ccc(-c3ccccc3)cc1)CO2 | Cc1c(C)c2c(c(C)c1N)C(c1ccc(-c3ccccc3)cc1)CO2 | null | null | CCCCCC | Deprotection | OtherReaction | 93c46c2f9981b731115295839d7158a8a73faedd00707b7604ace2fa5f580cbc | f6571fb5b7780a2b467937abfba91ba7d787f19d503265f299ff4a25a08963bd | c1ccc(-c2ccc(C3COc4ccccc43)cc2)cc1 | [c:1]:[c:2](-[NH;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[NH2;D1;+0:3]-[c:2](:[c:1]):[c:4] | 89 | [{"value": 89.0, "product": "C1(=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)N)C)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-benzyl-3-(biphenyl-4-yl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-amine obtained in Reference Example 279, the title compound was synthesized in the same manner as in Reference Example 30. Yield 89%. Melting point: 149-150° C. (hexane).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in Ref... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | c1ccccc1 | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCO2 | Other | CCCCCC | null | null | Cc1c(C)c2c(c(C)c1NCc1ccccc1)C(c1ccc(-c3ccccc3)cc1)CO2>CCCCCC>Cc1c(C)c2c(c(C)c1N)C(c1ccc(-c3ccccc3)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2e94f2e99b4a4a5789fb996cddad873a | Cc1c(C)c2c(c(C)c1NCc1ccccc1)C(c1ccc(C3OCCO3)cc1)CO2>>Cc1c(C)c2c(c(C)c1N)C(c1ccc(C3OCCO3)cc1)CO2 | C(C1=CC=CC=C1)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C2OCCO2)C1C)C)C>>O1C(OCC1)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)N)C | c1ccc(C[NH:10][c:9]2[c:2]([CH3:1])[c:3]([CH3:4])[c:5]3[c:6]([c:7]2[CH3:8])[CH:11]([c:12]2[cH:13][cH:14][c:15]([CH:16]4[O:17][CH2:18][CH2:19][O:20]4)[cH:21][cH:22]2)[CH2:23][O:24]3)cc1>>[CH3:1][c:2]1[c:3]([CH3:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH2:10])[CH:11]([c:12]1[cH:13][cH:14][c:15]([CH:16]3[O:17][CH2:18][CH2:19][... | Cc1c(C)c2c(c(C)c1NCc1ccccc1)C(c1ccc(C3OCCO3)cc1)CO2 | Cc1c(C)c2c(c(C)c1N)C(c1ccc(C3OCCO3)cc1)CO2 | null | null | CCCCCC | Deprotection | OtherReaction | 93c46c2f9981b731115295839d7158a8a73faedd00707b7604ace2fa5f580cbc | f6571fb5b7780a2b467937abfba91ba7d787f19d503265f299ff4a25a08963bd | c1ccc2c(c1)OCC2c1ccc(C2OCCO2)cc1 | [c:1]:[c:2](-[NH;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[NH2;D1;+0:3]-[c:2](:[c:1]):[c:4] | 87 | [{"value": 87.0, "product": "O1C(OCC1)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)N)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-benzyl-3-(4-(1,3-dioxolan-2-yl)phenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-amine obtained in Reference Example 284, the title compound was synthesized in the same manner as in Reference Example 30. Yield 87%. Melting point: 125-136° C. (hexane).
Conditions: See reaction.notes.procedure_details.
Workup: o... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | c1ccccc1 | null | c1ccccc1.C1COCO1.c1ccc2c(c1)CCO2 | Other | CCCCCC | null | null | Cc1c(C)c2c(c(C)c1NCc1ccccc1)C(c1ccc(C3OCCO3)cc1)CO2>CCCCCC>Cc1c(C)c2c(c(C)c1N)C(c1ccc(C3OCCO3)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a7a51242f7d540918c1ea97fa072f57d | CCc1ccc(-c2coc3c(C)c(C)c(NCc4ccccc4)c(C)c23)cc1>>CCc1ccc(-c2coc3c(C)c(C)c(N)c(C)c23)cc1 | C(C1=CC=CC=C1)NC=1C(=C(C2=C(C(=CO2)C2=CC=C(C=C2)CC)C1C)C)C>>C(C)C1=CC=C(C=C1)C1=COC2=C1C(=C(C(=C2C)C)N)C | c1ccc(C[NH:16][c:15]2[c:13]([CH3:14])[c:11]([CH3:12])[c:10]3[o:9][cH:8][c:7](-[c:6]4[cH:5][cH:4][c:3]([CH2:2][CH3:1])[cH:21][cH:20]4)[c:19]3[c:17]2[CH3:18])cc1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][o:9][c:10]3[c:11]([CH3:12])[c:13]([CH3:14])[c:15]([NH2:16])[c:17]([CH3:18])[c:19]23)[cH:20][cH:21]1 | CCc1ccc(-c2coc3c(C)c(C)c(NCc4ccccc4)c(C)c23)cc1 | CCc1ccc(-c2coc3c(C)c(C)c(N)c(C)c23)cc1 | null | null | C(C)(=O)OCC.CCCCCC | Deprotection | OtherReaction | 93c46c2f9981b731115295839d7158a8a73faedd00707b7604ace2fa5f580cbc | f6571fb5b7780a2b467937abfba91ba7d787f19d503265f299ff4a25a08963bd | c1ccc(-c2coc3ccccc23)cc1 | [c:1]:[c:2](-[NH;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[NH2;D1;+0:3]-[c:2](:[c:1]):[c:4] | 85 | [{"value": 85.0, "product": "C(C)C1=CC=C(C=C1)C1=COC2=C1C(=C(C(=C2C)C)N)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-benzyl-3-(4-ethylphenyl)-4,6,7-trimethyl-1-benzofuran-5-amine obtained in Reference Example 281, the title compound was synthesized in the same manner as in Reference Example 30. Yield 85%. Melting point: 68-69° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in Ref... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | c1ccccc1 | null | c1ccccc1.c1ccc2occc2c1 | Other | C(C)(=O)OCC.CCCCCC | null | null | CCc1ccc(-c2coc3c(C)c(C)c(NCc4ccccc4)c(C)c23)cc1>C(C)(=O)OCC.CCCCCC>CCc1ccc(-c2coc3c(C)c(C)c(N)c(C)c23)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-90026062e9b244339663890062bcd45c | Cc1c(NCc2ccccc2)c(C)c2c(-c3ccc(C4CCCCC4)cc3)coc2c1C>>Cc1c(N)c(C)c2c(-c3ccc(C4CCCCC4)cc3)coc2c1C | C(C1=CC=CC=C1)NC=1C(=C(C2=C(C(=CO2)C2=CC=C(C=C2)C2CCCCC2)C1C)C)C>>C1(CCCCC1)C1=CC=C(C=C1)C1=COC2=C1C(=C(C(=C2C)C)N)C | c1ccc(C[NH:4][c:3]2[c:2]([CH3:1])[c:24]([CH3:25])[c:23]3[c:7]([c:5]2[CH3:6])[c:8](-[c:9]2[cH:10][cH:11][c:12]([CH:13]4[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]4)[cH:19][cH:20]2)[cH:21][o:22]3)cc1>>[CH3:1][c:2]1[c:3]([NH2:4])[c:5]([CH3:6])[c:7]2[c:8](-[c:9]3[cH:10][cH:11][c:12]([CH:13]4[CH2:14][CH2:15][CH2:16][CH2:17][CH... | Cc1c(NCc2ccccc2)c(C)c2c(-c3ccc(C4CCCCC4)cc3)coc2c1C | Cc1c(N)c(C)c2c(-c3ccc(C4CCCCC4)cc3)coc2c1C | null | null | CCCCCC | Deprotection | OtherReaction | 93c46c2f9981b731115295839d7158a8a73faedd00707b7604ace2fa5f580cbc | f6571fb5b7780a2b467937abfba91ba7d787f19d503265f299ff4a25a08963bd | c1ccc2c(-c3ccc(C4CCCCC4)cc3)coc2c1 | [c:1]:[c:2](-[NH;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[NH2;D1;+0:3]-[c:2](:[c:1]):[c:4] | 79 | [{"value": 79.0, "product": "C1(CCCCC1)C1=CC=C(C=C1)C1=COC2=C1C(=C(C(=C2C)C)N)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-benzyl-3-(4-cyclohexylphenyl)-4,6,7-trimethyl-1-benzofuran-5-amine obtained in Reference Example 283, the title compound was synthesized in the same manner as in Reference Example 30. Yield 79%. Melting point: 139-140° C. (hexane).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in Reference ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | c1ccccc1 | null | c1ccccc1.C1CCCCC1.c1ccc2occc2c1 | Other | CCCCCC | null | null | Cc1c(NCc2ccccc2)c(C)c2c(-c3ccc(C4CCCCC4)cc3)coc2c1C>CCCCCC>Cc1c(N)c(C)c2c(-c3ccc(C4CCCCC4)cc3)coc2c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-79add57daf0d4161ae95394668b54740 | CCc1ccc(-c2coc3c(C)c(C)c(N)c(C)c23)cc1>>CCc1ccc(C2COc3c(C)c(C)c(N)c(C)c32)cc1 | C(C)C1=CC=C(C=C1)C1=COC2=C1C(=C(C(=C2C)C)N)C>>C(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)N)C | [CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][o:9][c:10]3[c:11]([CH3:12])[c:13]([CH3:14])[c:15]([NH2:16])[c:17]([CH3:18])[c:19]23)[cH:20][cH:21]1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH:7]2[CH2:8][O:9][c:10]3[c:11]([CH3:12])[c:13]([CH3:14])[c:15]([NH2:16])[c:17]([CH3:18])[c:19]32)[cH:20][cH:21]1 | CCc1ccc(-c2coc3c(C)c(C)c(N)c(C)c23)cc1 | CCc1ccc(C2COc3c(C)c(C)c(N)c(C)c32)cc1 | null | null | CCCCCC | Reduction | OtherReaction | b86bd3f15ad056b18f24f98e80df6dc8108bba5322ef4250b69a51408c14b3cb | 7ece147c6909fe307632f67c21e1517a1747c8ff389dff4b19e644c711d1d84d | c1ccc(C2COc3ccccc32)cc1 | [c:1]:[c:2]1:[o;H0;D2;+0:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:11]:1:[c:12]>>[c:1]:[c:2]1:[c:11](:[c:12])-[CH;D3;+0:5](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10])-[CH2;D2;+0:4]-[O;H0;D2;+0:3]-1 | 80 | [{"value": 80.0, "product": "C(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)N)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3-(4-ethylphenyl)-4,6,7-trimethyl-1-benzofuran-5-amine obtained in Reference Example 311, the title compound was synthesized in the same manner as in Reference Example 144. Yield 80%. Melting point: 88-89° C. (hexane).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in Reference Example 311 | 10.6084/m9.figshare.5104873.v1 | null | null | Ether | c1ccc2occc2c1 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | null | CCCCCC | null | null | CCc1ccc(-c2coc3c(C)c(C)c(N)c(C)c23)cc1>CCCCCC>CCc1ccc(C2COc3c(C)c(C)c(N)c(C)c32)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4b9cae309f4342609c0094b549683f5d | Cc1c(C)c(NCc2ccccc2)c2c(c1C)C(c1ccc(C(C)C)cc1)CO2>>Cc1c(C)c(N)c2c(c1C)C(c1ccc(C(C)C)cc1)CO2 | C(C1=CC=CC=C1)NC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)C)C>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2N)C)C)C | c1ccc(C[NH:6][c:5]2[c:3]([CH3:4])[c:2]([CH3:1])[c:9]([CH3:10])[c:8]3[c:7]2[O:22][CH2:21][CH:11]3[c:12]2[cH:13][cH:14][c:15]([CH:16]([CH3:17])[CH3:18])[cH:19][cH:20]2)cc1>>[CH3:1][c:2]1[c:3]([CH3:4])[c:5]([NH2:6])[c:7]2[c:8]([c:9]1[CH3:10])[CH:11]([c:12]1[cH:13][cH:14][c:15]([CH:16]([CH3:17])[CH3:18])[cH:19][cH:20]1)[CH... | Cc1c(C)c(NCc2ccccc2)c2c(c1C)C(c1ccc(C(C)C)cc1)CO2 | Cc1c(C)c(N)c2c(c1C)C(c1ccc(C(C)C)cc1)CO2 | null | null | CCCCCC.C(C)(=O)OCC | Deprotection | OtherReaction | 93c46c2f9981b731115295839d7158a8a73faedd00707b7604ace2fa5f580cbc | f6571fb5b7780a2b467937abfba91ba7d787f19d503265f299ff4a25a08963bd | c1ccc(C2COc3ccccc32)cc1 | [#8:1]-[c:2]:[c:3](-[NH;D2;+0:4]-C-c1:c:c:c:c:c:1):[c:5]>>[#8:1]-[c:2]:[c:3](-[NH2;D1;+0:4]):[c:5] | 80 | [{"value": 80.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2N)C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-benzyl-3-(4-isopropylphenyl)-4,5,6-trimethyl-2,3-dihydro-1-benzofuran-7-amine synthesized in Reference Example 287, the title compound was synthesized in the same manner as in Reference Example 30. Yield 80%. Melting point: 122-123° C. (hexane-ethyl acetate).
Conditions: See reaction.notes.procedure_details.
Wo... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)CCO2 | Other | CCCCCC.C(C)(=O)OCC | null | null | Cc1c(C)c(NCc2ccccc2)c2c(c1C)C(c1ccc(C(C)C)cc1)CO2>CCCCCC.C(C)(=O)OCC>Cc1c(C)c(N)c2c(c1C)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5834f49bd2a14851a3a619d5714d26e7 | Cc1c(NCc2ccccc2)c2c(c3c1C(c1ccc(C(C)C)cc1)CO3)CCCC2>>Cc1c(N)c2c(c3c1C(c1ccc(C(C)C)cc1)CO3)CCCC2 | C(C1=CC=CC=C1)NC1=C(C2=C(OCC2C2=CC=C(C=C2)C(C)C)C=2CCCCC12)C>>C(C)(C)C1=CC=C(C=C1)C1C2=C(OC1)C=1CCCCC1C(=C2C)N | c1ccc(C[NH:4][c:3]2[c:2]([CH3:1])[c:8]3[c:7]([c:6]4[c:5]2[CH2:24][CH2:23][CH2:22][CH2:21]4)[O:20][CH2:19][CH:9]3[c:10]2[cH:11][cH:12][c:13]([CH:14]([CH3:15])[CH3:16])[cH:17][cH:18]2)cc1>>[CH3:1][c:2]1[c:3]([NH2:4])[c:5]2[c:6]([c:7]3[c:8]1[CH:9]([c:10]1[cH:11][cH:12][c:13]([CH:14]([CH3:15])[CH3:16])[cH:17][cH:18]1)[CH2:... | Cc1c(NCc2ccccc2)c2c(c3c1C(c1ccc(C(C)C)cc1)CO3)CCCC2 | Cc1c(N)c2c(c3c1C(c1ccc(C(C)C)cc1)CO3)CCCC2 | null | null | CCCCCC.C(C)(=O)OCC | Deprotection | OtherReaction | 93c46c2f9981b731115295839d7158a8a73faedd00707b7604ace2fa5f580cbc | f6571fb5b7780a2b467937abfba91ba7d787f19d503265f299ff4a25a08963bd | c1ccc(C2COc3c2ccc2c3CCCC2)cc1 | [c:1]:[c:2](-[NH;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[NH2;D1;+0:3]-[c:2](:[c:1]):[c:4] | 76 | [{"value": 76.0, "product": "C(C)(C)C1=CC=C(C=C1)C1C2=C(OC1)C=1CCCCC1C(=C2C)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-benzyl-3-(4-isopropylphenyl)-4-methyl-2,3,6,7,8,9-hexahydronaphtho[1,2-b]furan-5-amine synthesized in Reference Example 289, the title compound was synthesized in the same manner as in Reference Example 30. Yield 76%. Melting point: 106-107° C. (hexane-ethyl acetate).
Conditions: See reaction.notes.procedure_de... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | c1ccccc1 | null | c1ccccc1.c1cc2c(c3c1CCCC3)OCC2 | Other | CCCCCC.C(C)(=O)OCC | null | null | Cc1c(NCc2ccccc2)c2c(c3c1C(c1ccc(C(C)C)cc1)CO3)CCCC2>CCCCCC.C(C)(=O)OCC>Cc1c(N)c2c(c3c1C(c1ccc(C(C)C)cc1)CO3)CCCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8b83b66dda9d42d98e80b26992be70a8 | Cc1c(NCc2ccccc2)c2c(c3c1C(c1ccc(C(C)C)cc1)CO3)CCC2>>Cc1c(N)c2c(c3c1C(c1ccc(C(C)C)cc1)CO3)CCC2 | C(C1=CC=CC=C1)NC1=C(C2=C(OCC2C2=CC=C(C=C2)C(C)C)C=2CCCC12)C>>C(C)(C)C1=CC=C(C=C1)C1C2=C(OC1)C=1CCCC1C(=C2C)N | c1ccc(C[NH:4][c:3]2[c:2]([CH3:1])[c:8]3[c:7]([c:6]4[c:5]2[CH2:23][CH2:22][CH2:21]4)[O:20][CH2:19][CH:9]3[c:10]2[cH:11][cH:12][c:13]([CH:14]([CH3:15])[CH3:16])[cH:17][cH:18]2)cc1>>[CH3:1][c:2]1[c:3]([NH2:4])[c:5]2[c:6]([c:7]3[c:8]1[CH:9]([c:10]1[cH:11][cH:12][c:13]([CH:14]([CH3:15])[CH3:16])[cH:17][cH:18]1)[CH2:19][O:20... | Cc1c(NCc2ccccc2)c2c(c3c1C(c1ccc(C(C)C)cc1)CO3)CCC2 | Cc1c(N)c2c(c3c1C(c1ccc(C(C)C)cc1)CO3)CCC2 | null | null | CCCCCC.C(C)(=O)OCC | Deprotection | OtherReaction | 93c46c2f9981b731115295839d7158a8a73faedd00707b7604ace2fa5f580cbc | f6571fb5b7780a2b467937abfba91ba7d787f19d503265f299ff4a25a08963bd | c1ccc(C2COc3c2ccc2c3CCC2)cc1 | [c:1]:[c:2](-[NH;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[NH2;D1;+0:3]-[c:2](:[c:1]):[c:4] | 91 | [{"value": 91.0, "product": "C(C)(C)C1=CC=C(C=C1)C1C2=C(OC1)C=1CCCC1C(=C2C)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-benzyl-3-(4-isopropylphenyl)-4-methyl-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-5-amine synthesized in Reference Example 290, the title compound was synthesized in the same manner as in Reference Example 30. Yield 91%. Melting point: 112-113° C. (hexane-ethyl acetate).
Conditions: See reaction.notes.procedure_de... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | c1ccccc1 | null | c1ccccc1.c1cc2c(c3c1CCC3)OCC2 | Other | CCCCCC.C(C)(=O)OCC | null | null | Cc1c(NCc2ccccc2)c2c(c3c1C(c1ccc(C(C)C)cc1)CO3)CCC2>CCCCCC.C(C)(=O)OCC>Cc1c(N)c2c(c3c1C(c1ccc(C(C)C)cc1)CO3)CCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7052b4344eca462baababaca72048de8 | Cc1c(C=O)c2c(c(C)c1NC=O)C(c1ccc(C(C)C)cc1)CO2.O>>CCOC(=O)/C=C/c1c(C)c(NC=O)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | C(=O)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC=O)C.O>>C(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)/C=C/C(=O)OCC)C | [CH3:1][CH:26]([CH3:2])[c:25]1[cH:24][cH:23][c:22]([CH:21]2[c:17]3[c:15]([CH3:16])[c:11]([NH:12][CH:13]=[O:14])[c:9]([CH3:10])[c:8]([CH:7]=[O:5])[c:18]3[O:19][CH2:20]2)[cH:30][cH:29]1.[OH2:3]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])/[CH:6]=[CH:7]/[c:8]1[c:9]([CH3:10])[c:11]([NH:12][CH:13]=[O:14])[c:15]([CH3:16])[c:17]2[c:18]1... | Cc1c(C=O)c2c(c(C)c1NC=O)C(c1ccc(C(C)C)cc1)CO2.O | CCOC(=O)/C=C/c1c(C)c(NC=O)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | null | null | null | Acylation | OtherReaction | 413a3b585345c86022625b69802bc39b9b259917155a84cd614fa1a2b5fc6016 | ddcf186a3b3d092bacf0764dd0ca53b0c2b1af686cadd4b34c9cceeb9942fb68 | c1ccc(C2COc3ccccc32)cc1 | [#8:1]-[c:2]:[c:3](-[CH;D2;+0:4]=[O;H0;D1;+0:5]):[c:6].[CH3;D1;+0:7]-[CH;D3;+0:8](-[CH3;D1;+0:9])-[c:10](:[c:11]):[c:12].[OH2;D0;+0:13]>>[#8:1]-[c:2]:[c:3](/[CH;D2;+0:4]=[C:14]/[C:15](=[O;H0;D1;+0:5])-[O;H0;D2;+0:13]-[CH2;D2;+0:9]-[CH3;D1;+0:7]):[c:6].[C;D1;H3:16]-[CH;D3;+0:8](-[C;D1;H3:17])-[c:10](:[c:11]):[c:12] | null | [] | null | null | 30 | MINUTE | To the reaction solution was added (7-formyl-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)formamide obtained in Example 60 (3.0 g, 8.89 mmol), and the mixture was stirred at room temperature for 30 minutes. Water was added to the reaction solution, and the product was extracted with diisopropyl ethe... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Ester | null | null | c1ccc2c(c1)CCO2.c1ccccc1 | Other | null | null | 0.5 | Cc1c(C=O)c2c(c(C)c1NC=O)C(c1ccc(C(C)C)cc1)CO2.O>>CCOC(=O)/C=C/c1c(C)c(NC=O)c(C)c2c1OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5ef7918283814704bb2b50ea56370c86 | CCOC(=O)CCc1c(C)c(N)c(C)c2c1OCC2c1ccc(C(C)C)cc1>>Cc1c(N)c(C)c2c(c1CCCO)OCC2c1ccc(C(C)C)cc1 | O.NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)CCC(=O)OCC)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)CCCO)C | CCO[C:12]([CH2:11][CH2:10][c:9]1[c:2]([CH3:1])[c:3]([NH2:4])[c:5]([CH3:6])[c:7]2[c:8]1[O:14][CH2:15][CH:16]2[c:17]1[cH:18][cH:19][c:20]([CH:21]([CH3:22])[CH3:23])[cH:24][cH:25]1)=[O:13]>>[CH3:1][c:2]1[c:3]([NH2:4])[c:5]([CH3:6])[c:7]2[c:8]([c:9]1[CH2:10][CH2:11][CH2:12][OH:13])[O:14][CH2:15][CH:16]2[c:17]1[cH:18][cH:19... | CCOC(=O)CCc1c(C)c(N)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | Cc1c(N)c(C)c2c(c1CCCO)OCC2c1ccc(C(C)C)cc1 | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(C2COc3ccccc32)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | 66 | [{"value": 66.0, "product": "NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)CCCO)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a suspension of ethyl 3-(5-amino-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-7-yl)propanoate synthesized in Reference Example 321 (1.28 g, 3.36 mmol) in THF, was added Lithium aluminum hydride (255 mg, 6.72 mmol) at 0° C., and the mixture was stirred at the same temperature for 30 minutes and heated ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccc2c(c1)CCO2.c1ccccc1 | HO- | C1CCOC1 | null | 0.5 | CCOC(=O)CCc1c(C)c(N)c(C)c2c1OCC2c1ccc(C(C)C)cc1>C1CCOC1>Cc1c(N)c(C)c2c(c1CCCO)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e25453950bd149adb42c91e7999b74e8 | Cc1c(N)cc2c(c1C)OCC2c1ccc(C(C)C)cc1.O=C1CCC(=O)N1Br>>Cc1c(C)c2c(c(Br)c1N)C(c1ccc(C(C)C)cc1)CO2 | C(C)(C)C1=CC=C(C=C1)C1COC2=C1C=C(C(=C2C)C)N.BrN1C(CCC1=O)=O>>BrC1=C(C(=C(C2=C1C(CO2)C2=CC=C(C=C2)C(C)C)C)C)N | [CH3:1][c:2]1[c:3]([CH3:4])[c:5]2[c:6]([cH:7][c:9]1[NH2:10])[CH:11]([c:12]1[cH:13][cH:14][c:15]([CH:16]([CH3:17])[CH3:18])[cH:19][cH:20]1)[CH2:21][O:22]2.O=C1CCC(=O)N1[Br:8]>>[CH3:1][c:2]1[c:3]([CH3:4])[c:5]2[c:6]([c:7]([Br:8])[c:9]1[NH2:10])[CH:11]([c:12]1[cH:13][cH:14][c:15]([CH:16]([CH3:17])[CH3:18])[cH:19][cH:20]1)... | Cc1c(N)cc2c(c1C)OCC2c1ccc(C(C)C)cc1.O=C1CCC(=O)N1Br | Cc1c(C)c2c(c(Br)c1N)C(c1ccc(C(C)C)cc1)CO2 | null | null | C(C)#N | Functional Group Interconversion | Bromination | 9d435b6d8ca3eb4960de979a7fab0da0b07ca71107a2372e1fc0a449c23e935f | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccc(C2COc3ccccc32)cc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#8:2]-[c:3]:[c:4](:[cH;D2;+0:5]:[c:6](-[N;D1;H2:7]):[c:8])-[C:9]>>[#8:2]-[c:3]:[c:4](:[c;H0;D3;+0:5](-[Br;H0;D1;+0:1]):[c:6](-[N;D1;H2:7]):[c:8])-[C:9] | 34 | [{"value": 34.0, "product": "BrC1=C(C(=C(C2=C1C(CO2)C2=CC=C(C=C2)C(C)C)C)C)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of 3-(4-isopropylphenyl)-6,7-dimethyl-2,3-dihydro-1-benzofuran-5-amine synthesized in Reference Example 31 (5.62 g, 21.1 mmol) in acetonitrile (60 mL), was added N-bromosuccinimide (3.76 g, 21.1 mmol) at −20° C., and the mixture was stirred at the same temperature for 10 minutes. The solvent was distilled... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccc2c(c1)CCO2.C1CCNC1 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | HO- | C(C)#N | null | 0.166667 | Cc1c(N)cc2c(c1C)OCC2c1ccc(C(C)C)cc1.O=C1CCC(=O)N1Br>C(C)#N>Cc1c(C)c2c(c(Br)c1N)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fefee18078de4832aaf5a4299aea070a | Cc1c(Br)c2c(c(C)c1NC=O)C(c1ccc(C(C)C)cc1)CO2.OB(O)c1ccccc1>>Cc1c(NC=O)c(C)c2c(c1-c1ccccc1)OCC2c1ccc(C(C)C)cc1 | BrC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC=O)C.C1(=CC=CC=C1)B(O)O.COCCOC>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C2=CC=CC=C2)C)NC=O)C | Br[c:11]1[c:2]([CH3:1])[c:3]([NH:4][CH:5]=[O:6])[c:7]([CH3:8])[c:9]2[c:10]1[O:18][CH2:19][CH:20]2[c:21]1[cH:22][cH:23][c:24]([CH:25]([CH3:26])[CH3:27])[cH:28][cH:29]1.OB(O)[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][c:2]1[c:3]([NH:4][CH:5]=[O:6])[c:7]([CH3:8])[c:9]2[c:10]([c:11]1-[c:12]1[cH:13][cH:14][cH:15][c... | Cc1c(Br)c2c(c(C)c1NC=O)C(c1ccc(C(C)C)cc1)CO2.OB(O)c1ccccc1 | Cc1c(NC=O)c(C)c2c(c1-c1ccccc1)OCC2c1ccc(C(C)C)cc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C(C)(=O)OCC.C([O-])([O-])=O.[Na+].[Na+] | C-C Coupling | Suzuki coupling with boronic acids | 56c93a2f9806908798c499807b17d3f0e66e3ff1161f180dd511ec545b7e9634 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccc3c2OCC3c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2](:[c:3])-[#8:4]-[C:5]):[c:6](-[C;D1;H3:7]):[c:8].O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[C:5]-[#8:4]-[c:2](:[c:3]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]):[c:6](-[C;D1;H3:7]):[c:8] | null | [] | null | null | null | null | A mixture of (7-bromo-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)formamide obtained in Example 59 (1.0 g, 2.58 mmol), phenylboronic acid (345 mg, 2.83 mmol) and tetrakis(triphenylphosphine)palladium (99 mg, 0.086 mmol) in 2 N sodium carbonate aqueous solution (30 mL)-1,2-dimethoxyethane (15 mL) wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)CCO2.c1ccccc1 | c1ccccc1.c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2.c1ccccc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C(C)(=O)OCC.C([O-])([O-])=O.[Na+].[Na+] | null | null | Cc1c(Br)c2c(c(C)c1NC=O)C(c1ccc(C(C)C)cc1)CO2.OB(O)c1ccccc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C(C)(=O)OCC.C([O-])([O-])=O.[Na+].[Na+]>Cc1c(NC=O)c(C)c2c(c1-c1ccccc1)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-27a16d3093b34616b0498885dd16cae1 | Cc1c2c(c(C(C)(O)c3ccc(C(C)C)cc3)c(C)c1NC(=O)OC(C)(C)C)OCC2>>C=C(c1ccc(C(C)C)cc1)c1c(C)c(N)c(C)c2c1OCC2 | C(O)([O-])=O.[Na+].OC(C)(C1=CC=C(C=C1)C(C)C)C1=C(C(=C(C=2CCOC21)C)NC(OC(C)(C)C)=O)C.Cl.C(C)(=O)OCC>>C(C)(C)C1=CC=C(C=C1)C(=C)C1=C(C(=C(C=2CCOC21)C)N)C | CC(C)(C)OC(=O)[NH:16][c:15]1[c:13]([CH3:14])[c:12]([C:2](O)([CH3:1])[c:3]2[cH:4][cH:5][c:6]([CH:7]([CH3:8])[CH3:9])[cH:10][cH:11]2)[c:20]2[c:19]([c:17]1[CH3:18])[CH2:23][CH2:22][O:21]2>>[CH2:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([CH:7]([CH3:8])[CH3:9])[cH:10][cH:11]1)[c:12]1[c:13]([CH3:14])[c:15]([NH2:16])[c:17]([CH3:18])[c... | Cc1c2c(c(C(C)(O)c3ccc(C(C)C)cc3)c(C)c1NC(=O)OC(C)(C)C)OCC2 | C=C(c1ccc(C(C)C)cc1)c1c(C)c(N)c(C)c2c1OCC2 | null | null | C(C)(=O)OCC | Functional Group Interconversion | OtherReaction | 8efc65beabe725d6ec6a8b15cc9ab5f22cd8c8891c580b66fcbedc0fbdf38f0b | 80a4138e1a9c8c892fe18b4ebaddd220a5b31d9818e552008700aeebc4794d42 | C=C(c1ccccc1)c1cccc2c1OCC2 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5](-[C;H0;D4;+0:6](-O)(-[CH3;D1;+0:7])-[c:8](:[c:9]):[c:10]):[c:11]-[#8:12]>>[#8:12]-[c:11]:[c:5](-[C;H0;D3;+0:6](=[CH2;D1;+0:7])-[c:8](:[c:9]):[c:10]):[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | 99.8 | [{"value": 99.8, "product": "C(C)(C)C1=CC=C(C=C1)C(=C)C1=C(C(=C(C=2CCOC21)C)N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of tert-butyl (7-(1-hydroxy-1-(4-isopropylphenyl)ethyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)carbamate obtained in Example 223 (306 mg, 0.72 mmol) in ethyl acetate (5 mL) was added dropwise a solution of 4 N hydrochloric acid-ethyl acetate (5 mL) under ice-cooling, and the reaction solution was stir... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Tertiary alcohol.Boc | Primary amine.Vinyl | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | HO- | C(C)(=O)OCC | null | 0.5 | Cc1c2c(c(C(C)(O)c3ccc(C(C)C)cc3)c(C)c1NC(=O)OC(C)(C)C)OCC2>C(C)(=O)OCC>C=C(c1ccc(C(C)C)cc1)c1c(C)c(N)c(C)c2c1OCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-22119f0b002e4cb19e673de2eefb96e3 | COc1cc(C)c(N(Cc2ccccc2)C(=O)CC(C)(C)C)c(C)c1Cc1ccc(C(C)C)cc1>>Cc1cc(O)c(Cc2ccc(C(C)C)cc2)c(C)c1N(Cc1ccccc1)C(=O)CC(C)(C)C | C(C1=CC=CC=C1)N(C(CC(C)(C)C)=O)C1=C(C(=C(C=C1C)OC)CC1=CC=C(C=C1)C(C)C)C>>C(C1=CC=CC=C1)N(C(CC(C)(C)C)=O)C1=C(C(=C(C=C1C)O)CC1=CC=C(C=C1)C(C)C)C | C[O:5][c:4]1[cH:3][c:2]([CH3:1])[c:19]([N:20]([CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[C:28](=[O:29])[CH2:30][C:31]([CH3:32])([CH3:33])[CH3:34])[c:17]([CH3:18])[c:6]1[CH2:7][c:8]1[cH:9][cH:10][c:11]([CH:12]([CH3:13])[CH3:14])[cH:15][cH:16]1>>[CH3:1][c:2]1[cH:3][c:4]([OH:5])[c:6]([CH2:7][c:8]2[cH:9][cH:10][c... | COc1cc(C)c(N(Cc2ccccc2)C(=O)CC(C)(C)C)c(C)c1Cc1ccc(C(C)C)cc1 | Cc1cc(O)c(Cc2ccc(C(C)C)cc2)c(C)c1N(Cc1ccccc1)C(=O)CC(C)(C)C | null | null | C(C)(=O)OCC.CCCCCC | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(CNc2cccc(Cc3ccccc3)c2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 83 | [{"value": 83.0, "product": "C(C1=CC=CC=C1)N(C(CC(C)(C)C)=O)C1=C(C(=C(C=C1C)O)CC1=CC=C(C=C1)C(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-benzyl-N-(3-(4-isopropylbenzyl)-4-methoxy-2,6-dimethylphenyl)-3,3-dimethylbutanamide obtained in Reference Example 332, the title compound was synthesized in the same manner as in Reference Example 335. Yield 83%. Melting point: 167-168° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_detail... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | Other | C(C)(=O)OCC.CCCCCC | null | null | COc1cc(C)c(N(Cc2ccccc2)C(=O)CC(C)(C)C)c(C)c1Cc1ccc(C(C)C)cc1>C(C)(=O)OCC.CCCCCC>Cc1cc(O)c(Cc2ccc(C(C)C)cc2)c(C)c1N(Cc1ccccc1)C(=O)CC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-996d181b06ba4381bdb6fc9d4139cd59 | CC(=O)c1c(C)c(NC=O)c(C)c2c1OCC2c1ccc(C(C)C)cc1>>CC(=O)c1c(C)c(N)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | C([O-])(O)=O.[Na+].C(C)(=O)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC=O)C.Cl>>C(C)(=O)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)N)C | O=C[NH:8][c:7]1[c:5]([CH3:6])[c:4]([C:2]([CH3:1])=[O:3])[c:12]2[c:11]([c:9]1[CH3:10])[CH:15]([c:16]1[cH:17][cH:18][c:19]([CH:20]([CH3:21])[CH3:22])[cH:23][cH:24]1)[CH2:14][O:13]2>>[CH3:1][C:2](=[O:3])[c:4]1[c:5]([CH3:6])[c:7]([NH2:8])[c:9]([CH3:10])[c:11]2[c:12]1[O:13][CH2:14][CH:15]2[c:16]1[cH:17][cH:18][c:19]([CH:20]... | CC(=O)c1c(C)c(NC=O)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | CC(=O)c1c(C)c(N)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | null | null | CO | Reduction | Reduction of primary amides to amines | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1ccc(C2COc3ccccc32)cc1 | O=C-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | N-(7-Acetyl-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)formamide obtained in Example 203 (808 mg, 2.3 mmol) was added to a solution of methanol (10 mL) and concentrated hydrochloric acid (5 mL), and the mixture was heated under reflux for 2 hours. The reaction solution was cooled to room temperatu... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccc2c(c1)CCO2.c1ccccc1 | Other | CO | null | null | CC(=O)c1c(C)c(NC=O)c(C)c2c1OCC2c1ccc(C(C)C)cc1>CO>CC(=O)c1c(C)c(N)c(C)c2c1OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a33c9bd9d05e424e90fc89dea2a18ba7 | Cc1cc(C)c(C)c(OC(C)C(=O)c2ccc(C(C)C)cc2)c1>>Cc1cc(C)c2c(-c3ccc(C(C)C)cc3)c(C)oc2c1C | C(C)(C)C1=CC=C(C=C1)C(C(C)OC1=C(C(=CC(=C1)C)C)C)=O>>C(C)(C)C1=CC=C(C=C1)C1=C(OC2=C1C(=CC(=C2C)C)C)C | O=[C:7]([c:8]1[cH:9][cH:10][c:11]([CH:12]([CH3:13])[CH3:14])[cH:15][cH:16]1)[CH:17]([CH3:18])[O:19][c:20]1[cH:6][c:4]([CH3:5])[cH:3][c:2]([CH3:1])[c:21]1[CH3:22]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:7](-[c:8]3[cH:9][cH:10][c:11]([CH:12]([CH3:13])[CH3:14])[cH:15][cH:16]3)[c:17]([CH3:18])[o:19][c:20]2[c:21]1[CH3:22... | Cc1cc(C)c(C)c(OC(C)C(=O)c2ccc(C(C)C)cc2)c1 | Cc1cc(C)c2c(-c3ccc(C(C)C)cc3)c(C)oc2c1C | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 41440ef63bdcad0549de493ff63648d9e9e6255c65e521389e251312ab757f94 | a162075685c9eb50256a00ee0ecfa14ba2a448fd0344b073a356637e7fa80d08 | c1ccc(-c2coc3ccccc23)cc1 | O=[C;H0;D3;+0:1](-[CH;D3;+0:2](-[C;D1;H3:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8](-[C;D1;H3:9]):[c:10])-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]>>[C;D1;H3:3]-[c;H0;D3;+0:2]1:[o;H0;D2;+0:4]:[c:5](:[c:6]):[c;H0;D3;+0:7](:[c:8](-[C;D1;H3:9]):[c:10]):[c;H0;D3;+0:1]:1-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[... | 96 | [{"value": 96.0, "product": "C(C)(C)C1=CC=C(C=C1)C1=C(OC2=C1C(=CC(=C2C)C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A mixed solution of 1-(4-isopropylphenyl)-2-(2,3,5-trimethylphenoxy)propan-1-one obtained in Reference Example 346 (61.3 g, 194 mmol), Amberlyst 15 (61.0 g) and a molecular sieve MS 4A (30 g) in toluene (200 mL) was heated under reflux at 80° C. for 2 hours. The reaction solution was filtered through celite, and the fi... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether | null | c1ccccc1 | c1ccc2occc2c1 | c1ccccc1.c1ccc2occc2c1 | HO- | C1(=CC=CC=C1)C | 80 | null | Cc1cc(C)c(C)c(OC(C)C(=O)c2ccc(C(C)C)cc2)c1>C1(=CC=CC=C1)C>Cc1cc(C)c2c(-c3ccc(C(C)C)cc3)c(C)oc2c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0b7311d1858b4da49fadfa2cbd106969 | Cc1cc(C)c2c(-c3ccc(C(C)C)cc3)c(C)oc2c1C>>Cc1cc(C)c2c(c1C)O[C@@H](C)[C@H]2c1ccc(C(C)C)cc1 | C(C)(C)C1=CC=C(C=C1)C1=C(OC2=C1C(=CC(=C2C)C)C)C>>C(C)(C)C1=CC=C(C=C1)[C@@H]1[C@@H](OC2=C1C(=CC(=C2C)C)C)C | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:7]([c:8]1[CH3:9])[o:10][c:11]([CH3:12])[c:13]2-[c:14]1[cH:15][cH:16][c:17]([CH:18]([CH3:19])[CH3:20])[cH:21][cH:22]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:7]([c:8]1[CH3:9])[O:10][C@@H:11]([CH3:12])[C@H:13]2[c:14]1[cH:15][cH:16][c:17]([CH:18]([CH3:19])[CH3:20])[cH:21][cH:22... | Cc1cc(C)c2c(-c3ccc(C(C)C)cc3)c(C)oc2c1C | Cc1cc(C)c2c(c1C)O[C@@H](C)[C@H]2c1ccc(C(C)C)cc1 | null | null | CO | Reduction | OtherReaction | b86bd3f15ad056b18f24f98e80df6dc8108bba5322ef4250b69a51408c14b3cb | 7ece147c6909fe307632f67c21e1517a1747c8ff389dff4b19e644c711d1d84d | c1ccc([C@@H]2COc3ccccc32)cc1 | [C;D1;H3:1]-[c;H0;D3;+0:2]1:[o;H0;D2;+0:3]:[c:4](:[c:5]):[c:6](:[c:7]):[c;H0;D3;+0:8]:1-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[C;D1;H3:1]-[C@@H;D3;+0:2]1-[O;H0;D2;+0:3]-[c:4](:[c:5]):[c:6](:[c:7])-[C@@H;D3;+0:8]-1-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13] | 63 | [{"value": 63.0, "product": "C(C)(C)C1=CC=C(C=C1)[C@@H]1[C@@H](OC2=C1C(=CC(=C2C)C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3-(4-isopropylphenyl)-2,4,6,7-tetramethyl-1-benzofuran obtained in Reference Example 347, the title compound was synthesized in the same manner as in Reference Example 144. Yield 63%. Melting point: 79-80° C. (methanol).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in Reference Example 347 | 10.6084/m9.figshare.5104873.v1 | null | null | Ether | c1ccc2occc2c1 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | null | CO | null | null | Cc1cc(C)c2c(-c3ccc(C(C)C)cc3)c(C)oc2c1C>CO>Cc1cc(C)c2c(c1C)O[C@@H](C)[C@H]2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4147b1915ea54805a407883a61aa1b47 | Cc1c(C)c2c(c(C)c1NCc1ccccc1)[C@H](c1ccc(C(C)C)cc1)[C@H](C)O2>>Cc1c(C)c2c(c(C)c1N)[C@H](c1ccc(C(C)C)cc1)[C@H](C)O2 | C(C1=CC=CC=C1)NC=1C(=C(C2=C([C@@H]([C@@H](O2)C)C2=CC=C(C=C2)C(C)C)C1C)C)C>>C(C)(C)C1=CC=C(C=C1)[C@@H]1[C@@H](OC2=C1C(=C(C(=C2C)C)N)C)C | c1ccc(C[NH:10][c:9]2[c:2]([CH3:1])[c:3]([CH3:4])[c:5]3[c:6]([c:7]2[CH3:8])[C@H:11]([c:12]2[cH:13][cH:14][c:15]([CH:16]([CH3:17])[CH3:18])[cH:19][cH:20]2)[C@H:21]([CH3:22])[O:23]3)cc1>>[CH3:1][c:2]1[c:3]([CH3:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH2:10])[C@H:11]([c:12]1[cH:13][cH:14][c:15]([CH:16]([CH3:17])[CH3:18])[cH:1... | Cc1c(C)c2c(c(C)c1NCc1ccccc1)[C@H](c1ccc(C(C)C)cc1)[C@H](C)O2 | Cc1c(C)c2c(c(C)c1N)[C@H](c1ccc(C(C)C)cc1)[C@H](C)O2 | null | null | CCCCCC | Deprotection | OtherReaction | 93c46c2f9981b731115295839d7158a8a73faedd00707b7604ace2fa5f580cbc | f6571fb5b7780a2b467937abfba91ba7d787f19d503265f299ff4a25a08963bd | c1ccc([C@@H]2COc3ccccc32)cc1 | [c:1]:[c:2](-[NH;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[NH2;D1;+0:3]-[c:2](:[c:1]):[c:4] | 83 | [{"value": 83.0, "product": "C(C)(C)C1=CC=C(C=C1)[C@@H]1[C@@H](OC2=C1C(=C(C(=C2C)C)N)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using (cis)-3-(4-isopropylphenyl)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran obtained in Reference Example 349, (cis)-5-bromo-3-(4-isopropylphenyl)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran was synthesized in the same manner as in Reference Example 23. Using this compound, (cis)-N-benzyl-3-(4-isopropylphenyl)-2,4,... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)CCO2 | Other | CCCCCC | null | null | Cc1c(C)c2c(c(C)c1NCc1ccccc1)[C@H](c1ccc(C(C)C)cc1)[C@H](C)O2>CCCCCC>Cc1c(C)c2c(c(C)c1N)[C@H](c1ccc(C(C)C)cc1)[C@H](C)O2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-02429486b0574ddb940d47953e93a712 | Cc1cc(C)cc(O)c1.O=C(CBr)c1ccccc1>>Cc1cc(C)cc(OCC(=O)c2ccccc2)c1 | CC=1C=C(C=C(C1)C)O.C(C(=O)C1=CC=CC=C1)Br>>CC=1C=C(OCC(=O)C2=CC=CC=C2)C=C(C1)C | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[cH:6][c:7]([OH:8])[cH:18]1.Br[CH2:9][C:10](=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[cH:6][c:7]([O:8][CH2:9][C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18]1 | Cc1cc(C)cc(O)c1.O=C(CBr)c1ccccc1 | Cc1cc(C)cc(OCC(=O)c2ccccc2)c1 | null | null | CO | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 8060b8e1565497a5ddf79be1adfe74f552b31798797b8841753247b06bdd2051 | 8749b179916f131d393264a24309227dc6177f560726bed2d1f4567dc2ac63f5 | O=C(COc1ccccc1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:3]=[C:2](-[c:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | 86 | [{"value": 86.0, "product": "CC=1C=C(OCC(=O)C2=CC=CC=C2)C=C(C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3,5-dimethylphenol and phenacyl bromide, the title compound was synthesized in the same manner as in Reference Example 177. Yield 86%. Melting point: 104-105° C. (methanol).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Aromatic alcohol | Ketone.Ether | null | null | c1ccccc1.c1ccccc1 | HBr | CO | null | null | Cc1cc(C)cc(O)c1.O=C(CBr)c1ccccc1>CO>Cc1cc(C)cc(OCC(=O)c2ccccc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1fdb231df8ba493aa98d126919e24b2c | Cc1cc2c(c(C)c1NCc1ccccc1)C(c1ccccc1)CO2>>Cc1cc2c(c(C)c1N)C(c1ccccc1)CO2 | C(C1=CC=CC=C1)NC=1C(=CC2=C(C(CO2)C2=CC=CC=C2)C1C)C>>CC1=C(C(=CC2=C1C(CO2)C2=CC=CC=C2)C)N | c1ccc(C[NH:9][c:8]2[c:2]([CH3:1])[cH:3][c:4]3[c:5]([c:6]2[CH3:7])[CH:10]([c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:17][O:18]3)cc1>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([c:6]([CH3:7])[c:8]1[NH2:9])[CH:10]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[CH2:17][O:18]2 | Cc1cc2c(c(C)c1NCc1ccccc1)C(c1ccccc1)CO2 | Cc1cc2c(c(C)c1N)C(c1ccccc1)CO2 | null | null | C(C)(=O)OCC.CCCCCC | Deprotection | OtherReaction | 93c46c2f9981b731115295839d7158a8a73faedd00707b7604ace2fa5f580cbc | f6571fb5b7780a2b467937abfba91ba7d787f19d503265f299ff4a25a08963bd | c1ccc(C2COc3ccccc32)cc1 | [c:1]:[c:2](-[NH;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[NH2;D1;+0:3]-[c:2](:[c:1]):[c:4] | 84 | [{"value": 84.0, "product": "CC1=C(C(=CC2=C1C(CO2)C2=CC=CC=C2)C)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-benzyl-4,6-dimethyl-3-phenyl-2,3-dihydro-1-benzofuran-5-amine obtained in Reference Example 357, the title compound was synthesized in the same manner as in Reference Example 30. Yield 84%. Melting point: 127-128° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in R... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)CCO2 | Other | C(C)(=O)OCC.CCCCCC | null | null | Cc1cc2c(c(C)c1NCc1ccccc1)C(c1ccccc1)CO2>C(C)(=O)OCC.CCCCCC>Cc1cc2c(c(C)c1N)C(c1ccccc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1b7dce0033044ba0985e978926a1b968 | COc1ccc(CC(=O)O)cc1.Cc1ccc([C@@H]2c3c(C)c(N)c(C)c(C)c3OC2(C)C)cc1>>COc1ccc(CC(=O)Nc2c(C)c(C)c3c(c2C)[C@@H](c2ccc(C)cc2)C(C)(C)O3)cc1 | CC1(OC2=C([C@H]1C1=CC=C(C=C1)C)C(=C(C(=C2C)C)N)C)C.COC1=CC=C(C=C1)CC(=O)O>>COC1=CC=C(C=C1)CC(=O)NC=1C(=C(C2=C([C@H](C(O2)(C)C)C2=CC=C(C=C2)C)C1C)C)C | O[C:8]([CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:33][cH:32]1)=[O:9].[NH2:10][c:11]1[c:12]([CH3:13])[c:14]([CH3:15])[c:16]2[c:17]([c:18]1[CH3:19])[C@@H:20]([c:21]1[cH:22][cH:23][c:24]([CH3:25])[cH:26][cH:27]1)[C:28]([CH3:29])([CH3:30])[O:31]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][C:8](=[O:9])[NH:10][c:11]2[... | COc1ccc(CC(=O)O)cc1.Cc1ccc([C@@H]2c3c(C)c(N)c(C)c(C)c3OC2(C)C)cc1 | COc1ccc(CC(=O)Nc2c(C)c(C)c3c(c2C)[C@@H](c2ccc(C)cc2)C(C)(C)O3)cc1 | null | null | C(C)(=O)OCC.CCCCCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Cc1ccccc1)Nc1ccc2c(c1)[C@@H](c1ccccc1)CO2 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 74 | [{"value": 74.0, "product": "COC1=CC=C(C=C1)CC(=O)NC=1C(=C(C2=C([C@H](C(O2)(C)C)C2=CC=C(C=C2)C)C1C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using (+)-(3R)-2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-amine obtained in Reference Example 134 and -4-methoxyphenylacetic acid, the title compound was synthesized in the same manner as in Reference Example 359. Yield 74%. Melting point: 186-188° C. (ethyl acetate-hexane).
Conditions: See rea... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCO2 | HO- | C(C)(=O)OCC.CCCCCC | null | null | COc1ccc(CC(=O)O)cc1.Cc1ccc([C@@H]2c3c(C)c(N)c(C)c(C)c3OC2(C)C)cc1>C(C)(=O)OCC.CCCCCC>COc1ccc(CC(=O)Nc2c(C)c(C)c3c(c2C)[C@@H](c2ccc(C)cc2)C(C)(C)O3)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-83bd6f0e894f4ec18da70277769b3327 | COc1ccc(C(C)C(=O)O)cc1.Cc1ccc([C@@H]2c3c(C)c(N)c(C)c(C)c3OC2(C)C)cc1>>COc1ccc(CCC(=O)Nc2c(C)c(C)c3c(c2C)[C@@H](c2ccc(C)cc2)C(C)(C)O3)cc1 | CC1(OC2=C([C@H]1C1=CC=C(C=C1)C)C(=C(C(=C2C)C)N)C)C.COC1=CC=C(C=C1)C(C(=O)O)C.C(C)(=O)OCC.CCCCCC>>COC1=CC=C(C=C1)CCC(=O)NC=1C(=C(C2=C([C@H](C(O2)(C)C)C2=CC=C(C=C2)C)C1C)C)C | O[C:9]([CH:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:34][cH:33]1)[CH3:8])=[O:10].[NH2:11][c:12]1[c:13]([CH3:14])[c:15]([CH3:16])[c:17]2[c:18]([c:19]1[CH3:20])[C@@H:21]([c:22]1[cH:23][cH:24][c:25]([CH3:26])[cH:27][cH:28]1)[C:29]([CH3:30])([CH3:31])[O:32]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][C:9](=[O:10... | COc1ccc(C(C)C(=O)O)cc1.Cc1ccc([C@@H]2c3c(C)c(N)c(C)c(C)c3OC2(C)C)cc1 | COc1ccc(CCC(=O)Nc2c(C)c(C)c3c(c2C)[C@@H](c2ccc(C)cc2)C(C)(C)O3)cc1 | null | null | null | Acylation | OtherReaction | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CCc1ccccc1)Nc1ccc2c(c1)[C@@H](c1ccccc1)CO2 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3](-[CH3;D1;+0:4])-[c:5](:[c:6]):[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[CH2;D2;+0:4]-[CH2;D2;+0:3]-[c:5](:[c:6]):[c:7])-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 21 | [{"value": 21.0, "product": "COC1=CC=C(C=C1)CCC(=O)NC=1C(=C(C2=C([C@H](C(O2)(C)C)C2=CC=C(C=C2)C)C1C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using (+)-(3R)-2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-amine obtained in Reference Example 134 and -4-methoxyphenylpropionic acid, the title compound was synthesized in the same manner as in Reference Example 359. Yield 21%. Melting point: 170-172° C. (ethyl acetate-hexane).
Conditions: See ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCO2 | HO- | null | null | null | COc1ccc(C(C)C(=O)O)cc1.Cc1ccc([C@@H]2c3c(C)c(N)c(C)c(C)c3OC2(C)C)cc1>>COc1ccc(CCC(=O)Nc2c(C)c(C)c3c(c2C)[C@@H](c2ccc(C)cc2)C(C)(C)O3)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f9a20d0d047b4fa8ab2b22493c4b249d | COc1ccc(CC(=O)Nc2c(C)c(C)c3c(c2C)C(c2ccc(C(C)C)cc2)C(C)(C)O3)cc1>>COc1ccc(CCNc2c(C)c(C)c3c(c2C)C(c2ccc(C(C)C)cc2)C(C)(C)O3)cc1 | [OH-].[Na+].C(C)(C)C1=CC=C(C=C1)C1C(OC2=C1C(=C(C(=C2C)C)NC(CC2=CC=C(C=C2)OC)=O)C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-]>>C(C)(C)C1=CC=C(C=C1)C1C(OC2=C1C(=C(C(=C2C)C)NCCC2=CC=C(C=C2)OC)C)(C)C | O=[C:8]([CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:34][cH:33]1)[NH:9][c:10]1[c:11]([CH3:12])[c:13]([CH3:14])[c:15]2[c:16]([c:17]1[CH3:18])[CH:19]([c:20]1[cH:21][cH:22][c:23]([CH:24]([CH3:25])[CH3:26])[cH:27][cH:28]1)[C:29]([CH3:30])([CH3:31])[O:32]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][NH:9][c:10]2[... | COc1ccc(CC(=O)Nc2c(C)c(C)c3c(c2C)C(c2ccc(C(C)C)cc2)C(C)(C)O3)cc1 | COc1ccc(CCNc2c(C)c(C)c3c(c2C)C(c2ccc(C(C)C)cc2)C(C)(C)O3)cc1 | null | null | C1CCOC1 | Reduction | Reduction of secondary amides to amines | 85b757f1833edc9e5c6365ee6b904683f414e7b9a5f9bfcfd7addca401447058 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc(CCNc2ccc3c(c2)C(c2ccccc2)CO3)cc1 | O=[C;H0;D3;+0:1](-[#7:2]-[c:3])-[C:4]-[c:5]>>[c:3]-[#7:2]-[CH2;D2;+0:1]-[C:4]-[c:5] | 43 | [{"value": 43.0, "product": "C(C)(C)C1=CC=C(C=C1)C1C(OC2=C1C(=C(C(=C2C)C)NCCC2=CC=C(C=C2)OC)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a suspension of aluminum chloride (1.23 g, 9.25 mmol) in THF (40 mL) was slowly added lithium aluminium hydride (354 mg, 9.31 mmol) with ice-cooling, and the mixture was stirred at the same temperature for 10 minutes. To this mixture was added N-(3-(4-isopropylphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCO2 | Other | C1CCOC1 | null | 0.166667 | COc1ccc(CC(=O)Nc2c(C)c(C)c3c(c2C)C(c2ccc(C(C)C)cc2)C(C)(C)O3)cc1>C1CCOC1>COc1ccc(CCNc2c(C)c(C)c3c(c2C)C(c2ccc(C(C)C)cc2)C(C)(C)O3)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ec91371f9a8143ea85e3d45f5fe0d9ed | Cc1c(C)c2c(c(C)c1N)C(C)(c1ccc(C(C)C)cc1)CO2>>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(C)(c1ccc(C(C)C)cc1)CO2 | C(C)(C)C1=CC=C(C=C1)C1(COC2=C1C(=C(C(=C2C)C)N)C)C>>C(C)(C)C1=CC=C(C=C1)C1(COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C)C | [CH3:1][c:2]1[c:3]([CH3:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH2:10])[C:18]([CH3:19])([c:20]1[cH:21][cH:22][c:23]([CH:24]([CH3:11])[CH3:13])[cH:27][cH:28]1)[CH2:29][O:12]2>>[CH3:1][c:2]1[c:3]([CH3:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH:10][C:11](=[O:12])[CH2:13][C:14]([CH3:15])([CH3:16])[CH3:17])[C:18]([CH3:19])([c:20]1... | Cc1c(C)c2c(c(C)c1N)C(C)(c1ccc(C(C)C)cc1)CO2 | Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(C)(c1ccc(C(C)C)cc1)CO2 | null | null | C(C)(=O)OCC.CCCCCC | Functional Group Addition | OtherReaction | 8fadbd9cef21da918c489cd3bc07ac474a816b119ce43e7fe6e3bc1908b4b437 | 885d0df579926d2c85fc365aa33e9f2ef9b0417804bd06587d82626e3522de9e | c1ccc(C2COc3ccccc32)cc1 | [C;D1;H3:1]-[C:2]1(-[c:3])-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-[c;H0;D3;+0:6]2:[c:7](-[C;D1;H3:8]):[c:9]:[c:10](-[NH2;D1;+0:11]):[c:12]:[c:13]:2-1.[CH3;D1;+0:14]-[CH;D3;+0:15](-[CH3;D1;+0:16])-[c:17](:[c:18]):[c:19]>>[C;D1;H3:20]-[CH;D3;+0:15](-[C;D1;H3:21])-[c:17](:[c:18]):[c:19].[C;D1;H3:22]-[C:23](-[C;D1;H3:24])(-[C;D1;H3:... | 37 | [{"value": 37.0, "product": "C(C)(C)C1=CC=C(C=C1)C1(COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3-(4-isopropylphenyl)-3,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-amine obtained in Reference Example 34, the title compound was synthesized in the same manner as in Example 1. Yield: 37%. Melting point: 194-195° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in R... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Ether.Secondary amide | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | Other | C(C)(=O)OCC.CCCCCC | null | null | Cc1c(C)c2c(c(C)c1N)C(C)(c1ccc(C(C)C)cc1)CO2>C(C)(=O)OCC.CCCCCC>Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(C)(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d20509fd09234d88852c8a636e8a4faa | Cc1c(N)cc2c(c1C)OCC2(C)c1ccc(C(C)C)cc1>>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OCC2(C)c1ccc(C(C)C)cc1 | C(C)(C)C1=CC=C(C=C1)C1(COC2=C1C=C(C(=C2C)C)N)C>>C(C)(C)C1=CC=C(C=C1)C1(COC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)C | [CH3:1][c:2]1[c:3]([NH2:4])[cH:12][c:13]2[c:14]([c:15]1[CH3:16])[O:6][CH2:18][C:19]2([CH3:20])[c:21]1[cH:22][cH:23][c:24]([CH:25]([CH3:5])[CH3:7])[cH:28][cH:29]1>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][c:13]2[c:14]([c:15]1[CH3:16])[O:17][CH2:18][C:19]2([CH3:20])[c:21]1[cH:... | Cc1c(N)cc2c(c1C)OCC2(C)c1ccc(C(C)C)cc1 | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OCC2(C)c1ccc(C(C)C)cc1 | null | null | C(C)(=O)OCC.CCCCCC | Functional Group Addition | OtherReaction | 8fadbd9cef21da918c489cd3bc07ac474a816b119ce43e7fe6e3bc1908b4b437 | 885d0df579926d2c85fc365aa33e9f2ef9b0417804bd06587d82626e3522de9e | c1ccc(C2COc3ccccc32)cc1 | [C;D1;H3:1]-[c:2]1:[c:3]:[c:4](-[NH2;D1;+0:5]):[c:6]:[c:7]2:[c;H0;D3;+0:8]:1-[O;H0;D2;+0:9]-[CH2;D2;+0:10]-[C:11]-2(-[C;D1;H3:12])-[c:13].[CH3;D1;+0:14]-[CH;D3;+0:15](-[CH3;D1;+0:16])-[c:17](:[c:18]):[c:19]>>[C;D1;H3:20]-[CH;D3;+0:15](-[C;D1;H3:21])-[c:17](:[c:18]):[c:19].[C;D1;H3:22]-[C:23](-[C;D1;H3:24])(-[C;D1;H3:25... | 59 | [{"value": 59.0, "product": "C(C)(C)C1=CC=C(C=C1)C1(COC2=C1C=C(C(=C2C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3-(4-isopropylphenyl)-3,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-amine obtained in Reference Example 35, the title compound was synthesized in the same manner as in Example 1. Yield: 59%. Melting point: 132-133° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details.
Workup: obtained in Refer... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Ether.Secondary amide | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | Other | C(C)(=O)OCC.CCCCCC | null | null | Cc1c(N)cc2c(c1C)OCC2(C)c1ccc(C(C)C)cc1>C(C)(=O)OCC.CCCCCC>Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OCC2(C)c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b6d3c1a6171340e4a0e6900283c66620 | CCOC(=O)C(=O)Nc1c(C)c(C)c2c(c1C)C(c1ccc(C(C)C)cc1)CO2.C[C](C)(C)[Mg][Cl]>>Cc1c(C)c2c(c(C)c1NC(=O)C(=O)C(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(C(=O)OCC)=O)C.C(C)(C)(C)[Mg]Cl>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(C(C(C)(C)C)=O)=O)C | CCO[C:13]([C:11]([NH:10][c:9]1[c:2]([CH3:1])[c:3]([CH3:4])[c:5]2[c:6]([c:7]1[CH3:8])[CH:19]([c:20]1[cH:21][cH:22][c:23]([CH:24]([CH3:25])[CH3:26])[cH:27][cH:28]1)[CH2:29][O:30]2)=[O:12])=[O:14].[Cl][Mg][C:15]([CH3:16])([CH3:17])[CH3:18]>>[CH3:1][c:2]1[c:3]([CH3:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH:10][C:11](=[O:12])[... | CCOC(=O)C(=O)Nc1c(C)c(C)c2c(c1C)C(c1ccc(C(C)C)cc1)CO2.C[C](C)(C)[Mg][Cl] | Cc1c(C)c2c(c(C)c1NC(=O)C(=O)C(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 8c9dfc377d301464c617227fe98631a4185f23c44c4f6504db15fcd7d9636acb | 9a0f66e31672299314bd1f514e8064bc73579c1dacd1558461f6f3dc476790ae | c1ccc(C2COc3ccccc32)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[O;D1;H0:4])-[#7:5]-[c:6].[C;D1;H3:7]-[C;H0;D4;+0:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[Mg]-[Cl]>>[C;D1;H3:7]-[C;H0;D4;+0:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[O;D1;H0:4])-[#7:5]-[c:6] | 28.5 | [{"value": 28.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(C(C(C)(C)C)=O)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 28.5, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(C(C(C)(C)C)=O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of ethyl (3-(4-isopropylphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-yl)oxamate (100 mg, 0.25 mmol) obtained in Example 15 in THF (3 ml) was added dropwise at 0° C. under an argon atmosphere tert-butylmagnesium chloride (2.0 M THF solution, 0.26 mL, 0.5 mmol) and the mixture was stirred for 30 minut... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ester | Ketone | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | HCl.Mg | C1CCOC1 | null | 0.5 | CCOC(=O)C(=O)Nc1c(C)c(C)c2c(c1C)C(c1ccc(C(C)C)cc1)CO2.C[C](C)(C)[Mg][Cl]>C1CCOC1>Cc1c(C)c2c(c(C)c1NC(=O)C(=O)C(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cb54d4d2920d46c0b967eae4cd70ff6c | CCC(=O)C(=O)O.Cc1c(C)c2c(c(C)c1N)C(c1ccc(C(C)C)cc1)CO2>>CCC(=O)C(=O)Nc1c(C)c(C)c2c(c1C)C(c1ccc(C(C)C)cc1)CO2 | C(C)N(CC)CC.C(C(=O)Cl)(=O)Cl.O=C(C(=O)O)CC.C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)N)C>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(C(CC)=O)=O)C | O[C:5]([C:3]([CH2:2][CH3:1])=[O:4])=[O:6].[NH2:7][c:8]1[c:9]([CH3:10])[c:11]([CH3:12])[c:13]2[c:14]([c:15]1[CH3:16])[CH:17]([c:18]1[cH:19][cH:20][c:21]([CH:22]([CH3:23])[CH3:24])[cH:25][cH:26]1)[CH2:27][O:28]2>>[CH3:1][CH2:2][C:3](=[O:4])[C:5](=[O:6])[NH:7][c:8]1[c:9]([CH3:10])[c:11]([CH3:12])[c:13]2[c:14]([c:15]1[CH3:... | CCC(=O)C(=O)O.Cc1c(C)c2c(c(C)c1N)C(c1ccc(C(C)C)cc1)CO2 | CCC(=O)C(=O)Nc1c(C)c(C)c2c(c1C)C(c1ccc(C(C)C)cc1)CO2 | null | CN(C)C=O | O.C1CCOC1 | Acylation | Carboxylic acid with primary amine to amide | 79db5ad9f3d1c798b49e3343b6cacedecc217b0543551ad418e0b2181685cff6 | d26dc0574345cfa45c01cee508bda74812ca7fa10a42dca7bf8a5fc4c9461f8c | c1ccc(C2COc3ccccc32)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])=[O;D1;H0:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:4]-[C:3](=[O;D1;H0:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 57 | [{"value": 57.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(C(CC)=O)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.6, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(C(CC)=O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 2-oxobutanoic acid (259 mg, 2.54 mmol) in THF (5 mL) was added dropwise with ice-cooling oxalyl chloride (0.33 mL, 3.80 mmol) and added DMF (three drops), and the mixture was stirred for 30 minutes. The reaction solution was warmed to room temperature and stirred at the same temperature for 1 hour, and... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone.Primary amine | Ketone.Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | HO- | CN(C)C=O.O.C1CCOC1 | null | 0.5 | CCC(=O)C(=O)O.Cc1c(C)c2c(c(C)c1N)C(c1ccc(C(C)C)cc1)CO2>CN(C)C=O.O.C1CCOC1>CCC(=O)C(=O)Nc1c(C)c(C)c2c(c1C)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3e07f111ffcd4018a26341d76e424da8 | CCC(=O)C(=O)Nc1c(C)c(C)c2c(c1C)C(c1ccc(C(C)C)cc1)CO2>>CCC(O)C(=O)Nc1c(C)c(C)c2c(c1C)C(c1ccc(C(C)C)cc1)CO2 | O.C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(C(CC)=O)=O)C.[BH4-].[Na+]>>OC(C(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C)C)CC | [CH3:1][CH2:2][C:3](=[O:4])[C:5](=[O:6])[NH:7][c:8]1[c:9]([CH3:10])[c:11]([CH3:12])[c:13]2[c:14]([c:15]1[CH3:16])[CH:17]([c:18]1[cH:19][cH:20][c:21]([CH:22]([CH3:23])[CH3:24])[cH:25][cH:26]1)[CH2:27][O:28]2>>[CH3:1][CH2:2][CH:3]([OH:4])[C:5](=[O:6])[NH:7][c:8]1[c:9]([CH3:10])[c:11]([CH3:12])[c:13]2[c:14]([c:15]1[CH3:16... | CCC(=O)C(=O)Nc1c(C)c(C)c2c(c1C)C(c1ccc(C(C)C)cc1)CO2 | CCC(O)C(=O)Nc1c(C)c(C)c2c(c1C)C(c1ccc(C(C)C)cc1)CO2 | null | null | CO | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(C2COc3ccccc32)cc1 | [C;D1;H3:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5](=[O;D1;H0:6])-[#7:7]-[c:8]>>[C;D1;H3:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[C:5](=[O;D1;H0:6])-[#7:7]-[c:8] | 72 | [{"value": 72.0, "product": "OC(C(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C)C)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.9, "product": "OC(C(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C)C)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of N-(3-(4-isopropylphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-yl)-2-oxobutanamide obtained in Example 17 (237 mg, 0.62 mmol) in methanol (5 mL) was added sodium borohydride (24 mg, 0.62 mmol) at 0° C. and the resulting mixture was stirred at room temperature for 30 minutes. Water was added to the... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | null | CO | null | 0.5 | CCC(=O)C(=O)Nc1c(C)c(C)c2c(c1C)C(c1ccc(C(C)C)cc1)CO2>CO>CCC(O)C(=O)Nc1c(C)c(C)c2c(c1C)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8362f4c4496f4443b0d0f67ead54cbe2 | CCOC(=O)C(=O)Nc1c(C)c(C)c2c(c1C)C(c1ccc(C(C)C)cc1)CO2.C[C](C)(C)[Mg][Cl]>>Cc1c(C)c2c(c(C)c1NC(=O)C(O)C(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(C(=O)OCC)=O)C.C(C)(C)(C)[Mg]Cl>>OC(C(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C)C)C(C)(C)C | CCO[C:13]([C:11]([NH:10][c:9]1[c:2]([CH3:1])[c:3]([CH3:4])[c:5]2[c:6]([c:7]1[CH3:8])[CH:19]([c:20]1[cH:21][cH:22][c:23]([CH:24]([CH3:25])[CH3:26])[cH:27][cH:28]1)[CH2:29][O:30]2)=[O:12])=[O:14].[Cl][Mg][C:15]([CH3:16])([CH3:17])[CH3:18]>>[CH3:1][c:2]1[c:3]([CH3:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH:10][C:11](=[O:12])[... | CCOC(=O)C(=O)Nc1c(C)c(C)c2c(c1C)C(c1ccc(C(C)C)cc1)CO2.C[C](C)(C)[Mg][Cl] | Cc1c(C)c2c(c(C)c1NC(=O)C(O)C(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | f11c602818d59fa2483317b4a048f3ff335f7488d21645f74ecbcf81671fe7cc | c13c7de77eea87cdfde3fdd079661598bd7d6088b2911e65a20cb590cca26e07 | c1ccc(C2COc3ccccc32)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](=[O;D1;H0:4])-[#7:5]-[c:6].[C;D1;H3:7]-[C;H0;D4;+0:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[Mg]-[Cl]>>[C;D1;H3:7]-[C;H0;D4;+0:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[CH;D3;+0:1](-[OH;D1;+0:2])-[C:3](=[O;D1;H0:4])-[#7:5]-[c:6] | 38 | [{"value": 38.0, "product": "OC(C(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C)C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.6, "product": "OC(C(=O)NC=1C(=C(C2=C(C(CO2)C2=CC=C(C=C2)C(C)C)C1C)C)C)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of ethyl (3-(4-isopropylphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-yl)oxamate (500 mg, 1.26 mmol) obtained in Example 15 in THF (10 mL) was added dropwise at 0° C. under an argon atmosphere tert-butylmagnesium chloride (2.0 M THF solution, 1.9 mL, 3.78 mmol) and the mixture was stirred for 30 minu... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ester | Secondary alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | HCl.Mg | C1CCOC1 | null | 0.5 | CCOC(=O)C(=O)Nc1c(C)c(C)c2c(c1C)C(c1ccc(C(C)C)cc1)CO2.C[C](C)(C)[Mg][Cl]>C1CCOC1>Cc1c(C)c2c(c(C)c1NC(=O)C(O)C(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-286bd2ebb28f4f19bcf72489f74230d3 | Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>>Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2)C)NC(CC(C)(C)C)=O)C.COC(Cl)Cl.O>>C(=O)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | [CH3:1][c:2]1[cH:3][c:6]2[c:7]([c:8]([CH3:9])[c:10]1[NH:11][C:12](=[O:13])[CH2:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH:19]([c:20]1[cH:21][cH:22][c:23]([CH:24]([CH3:25])[CH3:26])[cH:27][cH:28]1)[CH2:29][O:30]2>>[CH3:1][c:2]1[c:3]([CH:4]=[O:5])[c:6]2[c:7]([c:8]([CH3:9])[c:10]1[NH:11][C:12](=[O:13])[CH2:14][C:15]([CH3:1... | Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | null | [Ti](Cl)(Cl)(Cl)Cl | ClCCl | Miscellaneous | OtherReaction | c575f431b3127090be8382568230b261240de97350cb8e70e8cf496a0db5ebef | 3cccf922e74135722ee21a46ad7578302a8603e1f71d6f2113cd42de4ba0cf73 | c1ccc(C2COc3ccccc32)cc1 | [C:1]-[#8:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6](-[C;D1;H3:7]):[c:8]>>[C:1]-[#8:2]-[c:3](:[c:4]):[c;H0;D3;+0:5](-[C:9]=[O;D1;H0:10]):[c:6](-[C;D1;H3:7]):[c:8] | 75 | [{"value": 75.0, "product": "C(=O)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.6, "product": "C(=O)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To a solution of N-(3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (650 mg, 1.71 mmol) obtained in Example 3 and 1,1-dichloromethyl methyl ether (237 mg, 2.06 mmol) in dichloromethane (5 mL) was added dropwise at 0° C. under an argon atmosphere and ice-cooling titanium tetrachl... | 10.6084/m9.figshare.5104873.v1 | null | null | Aldehyde | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | Other | [Ti](Cl)(Cl)(Cl)Cl.ClCCl | null | 0.333333 | Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>[Ti](Cl)(Cl)(Cl)Cl.ClCCl>Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-659e1bbb5df541b9b024e0cf3ecf4449 | Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>>Cc1c(CO)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | C(=O)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.[BH4-].[Na+]>>OCC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | [CH3:1][c:2]1[c:3]([CH:4]=[O:5])[c:6]2[c:7]([c:8]([CH3:9])[c:10]1[NH:11][C:12](=[O:13])[CH2:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH:19]([c:20]1[cH:21][cH:22][c:23]([CH:24]([CH3:25])[CH3:26])[cH:27][cH:28]1)[CH2:29][O:30]2>>[CH3:1][c:2]1[c:3]([CH2:4][OH:5])[c:6]2[c:7]([c:8]([CH3:9])[c:10]1[NH:11][C:12](=[O:13])[CH2:14... | Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | Cc1c(CO)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | null | null | CO | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccc(C2COc3ccccc32)cc1 | [#8:1]-[c:2]:[c:3](-[CH;D2;+0:4]=[O;H0;D1;+0:5]):[c:6]>>[#8:1]-[c:2]:[c:3](-[CH2;D2;+0:4]-[OH;D1;+0:5]):[c:6] | 78 | [{"value": 78.0, "product": "OCC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.8, "product": "OCC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of N-(7-formyl-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (370 mg, 0.91 mmol) obtained in Example 20 in methanol (5 mL) was added sodium borohydride (34 mg, 0.91 mmol) at room temperature and the mixture was stirred for 1 hour. The reaction solution was concen... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | null | CO | null | 1 | Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>CO>Cc1c(CO)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-99982f16b8be41f7ad6055177d289e23 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(C)O)OCC2c1ccc(C(C)C)cc1>>CCc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | OC(C)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.FC(C(=O)O)(F)F.C(C)[SiH](CC)CC>>C(C)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | O[CH:2]([CH3:1])[c:3]1[c:4]([CH3:5])[c:6]([NH:7][C:8](=[O:9])[CH2:10][C:11]([CH3:12])([CH3:13])[CH3:14])[c:15]([CH3:16])[c:17]2[c:18]1[O:19][CH2:20][CH:21]2[c:22]1[cH:23][cH:24][c:25]([CH:26]([CH3:27])[CH3:28])[cH:29][cH:30]1>>[CH3:1][CH2:2][c:3]1[c:4]([CH3:5])[c:6]([NH:7][C:8](=[O:9])[CH2:10][C:11]([CH3:12])([CH3:13])... | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(C)O)OCC2c1ccc(C(C)C)cc1 | CCc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | null | null | null | Reduction | OtherReaction | 3c5af32aa639db2ebe4d9851942e9468e1838e06ae5b2c1669bca1d5e0922c33 | 46f8a11b80b06e754a5a34198d843342612a5e7ede950bda52ce3a500cedba0b | c1ccc(C2COc3ccccc32)cc1 | O-[CH;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[c:5]-[#8:6]>>[#8:6]-[c:5]:[c:3](-[CH2;D2;+0:1]-[C;D1;H3:2]):[c:4] | 52.2 | [{"value": 52.0, "product": "C(C)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.2, "product": "C(C)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a mixture of N-(7-(1-hydroxyethyl)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (200 mg, 0.47 mmol) obtained in Example 22 and trifluoroacetic acid (3 mL) was added under ice cooling triethylsilane (0.5 mL, 3.2 mmol) and the resulting mixture was stirred at room temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | null | null | c1ccc2c(c1)CCO2.c1ccccc1 | Other | null | null | 0.5 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(C)O)OCC2c1ccc(C(C)C)cc1>>CCc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e9271fda50144ec19e24166de76dec88 | CI.Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>>Cc1c(C)c(N(C)C(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | CI.C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)NC(CC(C)(C)C)=O)C.[H-].[Na+].O>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)N(C(CC(C)(C)C)=O)C)C | I[CH3:7].[CH3:1][c:2]1[c:3]([CH3:4])[c:5]([NH:6][C:8](=[O:9])[CH2:10][C:11]([CH3:12])([CH3:13])[CH3:14])[c:15]([CH3:16])[c:17]2[c:18]1[O:19][CH2:20][CH:21]2[c:22]1[cH:23][cH:24][c:25]([CH:26]([CH3:27])[CH3:28])[cH:29][cH:30]1>>[CH3:1][c:2]1[c:3]([CH3:4])[c:5]([N:6]([CH3:7])[C:8](=[O:9])[CH2:10][C:11]([CH3:12])([CH3:13]... | CI.Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | Cc1c(C)c(N(C)C(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 780d850c4b8333c4b07101ff526eea0725c627f5cbcabe141bddc514762f1fac | 0a16658309ac5595448433dd7ef49294830b145345df0b202ccd54727262e629 | c1ccc(C2COc3ccccc32)cc1 | I-[CH3;D1;+0:1].[C:2]-[C:3](=[O;D1;H0:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[C:2]-[C:3](=[O;D1;H0:4])-[N;H0;D3;+0:5](-[CH3;D1;+0:1])-[c:6](:[c:7]):[c:8] | 12 | [{"value": 12.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)N(C(CC(C)(C)C)=O)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 12.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2C)C)N(C(CC(C)(C)C)=O)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of N-(3-(4-isopropylphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (200 mg, 0.51 mmol) synthesized in Example 1 in DMF (3 mL) was added sodium hydride (a 60% dispersion in liquid paraffin, 24 mg, 0.6 mmol) at 0° C. and the resulting mixture was stirred at room temperature fo... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Tertiary amide | null | null | c1ccc2c(c1)CCO2.c1ccccc1 | HI | CN(C)C=O | null | 0.5 | CI.Cc1c(C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>CN(C)C=O>Cc1c(C)c(N(C)C(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-336e57978599436d984e5142471ca859 | C1CCNC1.Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>>Cc1c(CN2CCCC2)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | O.[BH4-].[Na+].N1CCCC1.C(=O)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2CN2CCCC2)C)NC(CC(C)(C)C)=O)C | [NH:5]1[CH2:6][CH2:7][CH2:8][CH2:9]1.O=[CH:4][c:3]1[c:2]([CH3:1])[c:14]([NH:15][C:16](=[O:17])[CH2:18][C:19]([CH3:20])([CH3:21])[CH3:22])[c:12]([CH3:13])[c:11]2[c:10]1[O:34][CH2:33][CH:23]2[c:24]1[cH:25][cH:26][c:27]([CH:28]([CH3:29])[CH3:30])[cH:31][cH:32]1>>[CH3:1][c:2]1[c:3]([CH2:4][N:5]2[CH2:6][CH2:7][CH2:8][CH2:9]... | C1CCNC1.Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | Cc1c(CN2CCCC2)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | null | CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4] | CO | Heteroatom Alkylation and Arylation | reductive amination | f320c54beea598cd731a01400cf9495fa26416685f3307ec69cb487e38cf79c3 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(C2COc3c(CN4CCCC4)cccc32)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]-[#8:5].[C:6]1-[C:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[#8:5]-[c:4]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:10]1-[C:6]-[C:7]-[C:8]-[C:9]-1):[c:3] | 49.6 | [{"value": 49.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2CN2CCCC2)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.6, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2CN2CCCC2)C)NC(CC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | To a solution of pyrrolidine (0.20 mL, 2.4 mmol) in methanol (5 mL) was added titanium tetraisopropoxide (0.36 mL, 1.20 mmol) and N-(7-formyl-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (250 mg; 0.61 mmol) obtained in Example 20 at 0° C. and the resulting mixture was stirred... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1.c1ccc2c(c1)CCO2 | Other | CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4].CO | null | 14 | C1CCNC1.Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4].CO>Cc1c(CN2CCCC2)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f25d27b319e8472c8ea2ffc40fbd8aa7 | CNC.Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>>Cc1c(CN(C)C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | C(=O)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.CNC>>CN(C)CC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | [NH:5]([CH3:6])[CH3:7].O=[CH:4][c:3]1[c:2]([CH3:1])[c:12]([NH:13][C:14](=[O:15])[CH2:16][C:17]([CH3:18])([CH3:19])[CH3:20])[c:10]([CH3:11])[c:9]2[c:8]1[O:32][CH2:31][CH:21]2[c:22]1[cH:23][cH:24][c:25]([CH:26]([CH3:27])[CH3:28])[cH:29][cH:30]1>>[CH3:1][c:2]1[c:3]([CH2:4][N:5]([CH3:6])[CH3:7])[c:8]2[c:9]([c:10]([CH3:11])... | CNC.Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | Cc1c(CN(C)C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | null | null | null | Heteroatom Alkylation and Arylation | reductive amination | 6d9c60e7c47e75322fc9565d992b855788f3516a27cb14d7f9ed299e190b30d3 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(C2COc3ccccc32)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]-[#8:5].[C;D1;H3:6]-[NH;D2;+0:7]-[C;D1;H3:8]>>[#8:5]-[c:4]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:7](-[C;D1;H3:6])-[C;D1;H3:8]):[c:3] | 37 | [{"value": 37.0, "product": "CN(C)CC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(7-formyl-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 20 and dimethylamine, the title compound was synthesized in the same manner as in Example 26. Yield: 37%. Amorphous substance.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | Other | null | null | null | CNC.Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>>Cc1c(CN(C)C)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d47f1cb63bdb40bf958c13e79a8d8f7f | Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(C)O)OCC2c1ccc(C(C)C)cc1 | C[Mg]Br.C(=O)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C>>OC(C)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | [CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[c:12]([CH3:13])[c:14]2[c:15]([c:16]1[CH:17]=[O:19])[O:20][CH2:21][CH:22]2[c:23]1[cH:24][cH:25][c:26]([CH:27]([CH3:28])[CH3:29])[cH:30][cH:31]1>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[c:12]([CH3:13])[c:... | Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(C)O)OCC2c1ccc(C(C)C)cc1 | null | null | O | Miscellaneous | OtherReaction | 1ffaf80f172e20da969364a5d2977299bc51b204f2262675c45c8ec58ff36ac0 | e005d650d08e61fc67b766830eb53235a9bc084cc3667d2f8a73c2fb8bb34277 | c1ccc(C2COc3ccccc32)cc1 | [#8:1]-[c:2]:[c:3](-[CH;D2;+0:4]=[O;H0;D1;+0:5]):[c:6]>>[#8:1]-[c:2]:[c:3](-[CH;D3;+0:4](-[C;D1;H3:7])-[OH;D1;+0:5]):[c:6] | 23.7 | [{"value": 19.0, "product": "OC(C)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 23.7, "product": "OC(C)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To methylmagnesium bromide (2.0 M THF solution, 5.0 mL, 10.0 mmol) was added N-(7-formyl-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (1.0 g, 1.91 mmol) obtained in Example 20 at 0° C. and the reaction solution was stirred at the same temperature for 1 hour. The reaction solu... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol | null | null | c1ccc2c(c1)CCO2.c1ccccc1 | Other | O | null | 1 | Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>O>Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(C)O)OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e459e874028d4392ab848ad9bf488a62 | Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>>CCC(O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | C(C)[Mg]Cl.C(=O)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C>>OC(CC)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | [CH:3](=[O:4])[c:5]1[c:6]([CH3:7])[c:8]([NH:9][C:10](=[O:11])[CH2:12][C:13]([CH3:14])([CH3:15])[CH3:16])[c:17]([CH3:18])[c:19]2[c:20]1[O:21][CH2:22][CH:23]2[c:24]1[cH:25][cH:26][c:27]([CH:28]([CH3:29])[CH3:30])[cH:31][cH:32]1>>[CH3:1][CH2:2][CH:3]([OH:4])[c:5]1[c:6]([CH3:7])[c:8]([NH:9][C:10](=[O:11])[CH2:12][C:13]([CH... | Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | CCC(O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | null | null | O | Miscellaneous | OtherReaction | 1ffaf80f172e20da969364a5d2977299bc51b204f2262675c45c8ec58ff36ac0 | e005d650d08e61fc67b766830eb53235a9bc084cc3667d2f8a73c2fb8bb34277 | c1ccc(C2COc3ccccc32)cc1 | [#8:1]-[c:2]:[c:3](-[CH;D2;+0:4]=[O;H0;D1;+0:5]):[c:6]>>[#8:1]-[c:2]:[c:3](-[CH;D3;+0:4](-[OH;D1;+0:5])-[C:7]-[C;D1;H3:8]):[c:6] | 35.1 | [{"value": 35.0, "product": "OC(CC)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.1, "product": "OC(CC)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To ethylmagnesium chloride (2.0 M THF solution, 5.0 mL, 10.0 mmol) was added N-(7-formyl-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (0.7 g, 1.72 mmol) obtained in Example 20 at 0° C. and the reaction solution was stirred at the same temperature for 1 hour. The reaction solu... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol | null | null | c1ccc2c(c1)CCO2.c1ccccc1 | Other | O | null | 1 | Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>O>CCC(O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0bf63b9fde694b7f9444f854b5865024 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(C)O)OCC2c1ccc(C(C)C)cc1>>CC(=O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | OC(C)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C>>C(C)(=O)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | [CH3:1][CH:2]([OH:3])[c:4]1[c:5]([CH3:6])[c:7]([NH:8][C:9](=[O:10])[CH2:11][C:12]([CH3:13])([CH3:14])[CH3:15])[c:16]([CH3:17])[c:18]2[c:19]1[O:20][CH2:21][CH:22]2[c:23]1[cH:24][cH:25][c:26]([CH:27]([CH3:28])[CH3:29])[cH:30][cH:31]1>>[CH3:1][C:2](=[O:3])[c:4]1[c:5]([CH3:6])[c:7]([NH:8][C:9](=[O:10])[CH2:11][C:12]([CH3:1... | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(C)O)OCC2c1ccc(C(C)C)cc1 | CC(=O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | null | [O-2].[O-2].[Mn+4] | null | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | c1ccc(C2COc3ccccc32)cc1 | [#8:1]-[c:2]:[c:3](-[CH;D3;+0:4](-[C;D1;H3:5])-[OH;D1;+0:6]):[c:7]>>[#8:1]-[c:2]:[c:3](-[C;H0;D3;+0:4](-[C;D1;H3:5])=[O;H0;D1;+0:6]):[c:7] | 76.2 | [{"value": 76.0, "product": "C(C)(=O)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.2, "product": "C(C)(=O)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 2 | HOUR | A mixture of N-(7-(1-hydroxyethyl)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (580 mg, 1.37 mmol) obtained in Example 22 and manganese dioxide (1.43 g, 16.4 mmol) were stirred at 100° C. for two hours. Insoluble materials were filtered off, and the filtrate was concentrated... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1ccc2c(c1)CCO2.c1ccccc1 | null | [O-2].[O-2].[Mn+4] | 100 | 2 | Cc1c(NC(=O)CC(C)(C)C)c(C)c2c(c1C(C)O)OCC2c1ccc(C(C)C)cc1>[O-2].[O-2].[Mn+4]>CC(=O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-293e86e028b74c6c9432d554dbe95219 | CC(=O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1.CCCCCC>>Cc1c(NC(=O)CC(C)(C)C)c(C)c(C(C)(C)O)c2c1C(c1ccc(C(C)C)cc1)CO2 | C(C)(=O)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.C(C)(=O)OCC.CCCCCC>>OC(C)(C)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | [CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[c:12]([CH3:13])[c:14]([C:15]([CH3:16])=[O:18])[c:19]2[c:20]1[CH:21]([c:22]1[cH:23][cH:24][c:25]([CH:26]([CH3:27])[CH3:28])[cH:29][cH:30]1)[CH2:31][O:32]2.CCCCC[CH3:17]>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH... | CC(=O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1.CCCCCC | Cc1c(NC(=O)CC(C)(C)C)c(C)c(C(C)(C)O)c2c1C(c1ccc(C(C)C)cc1)CO2 | null | null | null | C-C Coupling | OtherReaction | 2fffd6bd6bacb879d7ba2cf29351570d50899c51664d6359aa6c9ef1859cb5dd | 454f67ba8644982dc9f605915a0f36178771eadaffb50d3f1e0f17f2b6fdeb10 | c1ccc(C2COc3ccccc32)cc1 | C-C-C-C-C-[CH3;D1;+0:1].[#8:2]-[c:3]:[c:4](-[C;H0;D3;+0:5](-[C;D1;H3:6])=[O;H0;D1;+0:7]):[c:8]>>[#8:2]-[c:3]:[c:4](-[C;H0;D4;+0:5](-[C;D1;H3:6])(-[CH3;D1;+0:1])-[OH;D1;+0:7]):[c:8] | 34 | [{"value": 34.0, "product": "OC(C)(C)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using N-(7-acetyl-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 32, the title compound was synthesized in the same manner as in Example 22. Yield: 34%. Melting point: 133-134° C. (ethyl acetate-hexane).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | Other | null | null | null | CC(=O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1.CCCCCC>>Cc1c(NC(=O)CC(C)(C)C)c(C)c(C(C)(C)O)c2c1C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aec32b36ee7e48d7a3b185ae7add2df2 | CCC(O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1>>CCCc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | OC(CC)C1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2CCC)C)NC(CC(C)(C)C)=O)C | O[CH:3]([CH2:2][CH3:1])[c:4]1[c:5]([CH3:6])[c:7]([NH:8][C:9](=[O:10])[CH2:11][C:12]([CH3:13])([CH3:14])[CH3:15])[c:16]([CH3:17])[c:18]2[c:19]1[O:20][CH2:21][CH:22]2[c:23]1[cH:24][cH:25][c:26]([CH:27]([CH3:28])[CH3:29])[cH:30][cH:31]1>>[CH3:1][CH2:2][CH2:3][c:4]1[c:5]([CH3:6])[c:7]([NH:8][C:9](=[O:10])[CH2:11][C:12]([CH... | CCC(O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | CCCc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | null | null | C(C)(=O)OCC.CCCCCC | Reduction | OtherReaction | 3c5af32aa639db2ebe4d9851942e9468e1838e06ae5b2c1669bca1d5e0922c33 | 46f8a11b80b06e754a5a34198d843342612a5e7ede950bda52ce3a500cedba0b | c1ccc(C2COc3ccccc32)cc1 | O-[CH;D3;+0:1](-[C:2]-[C;D1;H3:3])-[c:4](:[c:5]):[c:6]-[#8:7]>>[#8:7]-[c:6]:[c:4](-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3]):[c:5] | 86 | [{"value": 86.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2CCC)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using a diastereo mixture of N-(7-(1-hydroxypropyl)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in the synthesis in Examples 30 and 31, the title compound was synthesized in the same manner as in Example 23. Yield: 86%. Melting point: 145-148° C. (ethyl acetate-hexa... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | null | null | c1ccc2c(c1)CCO2.c1ccccc1 | Other | C(C)(=O)OCC.CCCCCC | null | null | CCC(O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1>C(C)(=O)OCC.CCCCCC>CCCc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-06dcf45bfe5b4bf69f2f09a88345303c | Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.O=C1CCC(=O)N1Br>>Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | O.C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2)C)NC(CC(C)(C)C)=O)C.BrN1C(CCC1=O)=O>>BrC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | [CH3:1][c:2]1[cH:3][c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH:10][C:11](=[O:12])[CH2:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH:18]([c:19]1[cH:20][cH:21][c:22]([CH:23]([CH3:24])[CH3:25])[cH:26][cH:27]1)[CH2:28][O:29]2.O=C1CCC(=O)N1[Br:4]>>[CH3:1][c:2]1[c:3]([Br:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH:10][C:11](=[O:12])[CH2:13][... | Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.O=C1CCC(=O)N1Br | Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | null | null | C(C)#N | Functional Group Interconversion | Bromination | 9d435b6d8ca3eb4960de979a7fab0da0b07ca71107a2372e1fc0a449c23e935f | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccc(C2COc3ccccc32)cc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[C:2]-[#8:3]-[c:4](:[c:5]):[cH;D2;+0:6]:[c:7](-[C;D1;H3:8]):[c:9]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:6](:[c:7](-[C;D1;H3:8]):[c:9]):[c:4](:[c:5])-[#8:3]-[C:2] | 91.2 | [{"value": 91.0, "product": "BrC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.2, "product": "BrC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of N-(3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (1.0 g, 2.63 mmol) obtained in Example 3 in acetonitrile (30 mL) was added N-bromosuccinimide (468 mg, 2.63 mmol) at 0° C. and the reaction mixture was stirred at room temperature for 2 hours. Water was added to... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccc2c(c1)CCO2.C1CCNC1 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | HO- | C(C)#N | null | 2 | Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2.O=C1CCC(=O)N1Br>C(C)#N>Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-010f1a3bfe794fca84926ac9602d5b5b | CCOC(C)=O.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>>COc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | BrC1=C(C(=C(C=2C(COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.C(C)(=O)OCC.Cl>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2OC)C)NC(CC(C)(C)C)=O)C | CCO[C:1](C)=[O:2].Br[c:3]1[c:4]([CH3:5])[c:6]([NH:7][C:8](=[O:9])[CH2:10][C:11]([CH3:12])([CH3:13])[CH3:14])[c:15]([CH3:16])[c:17]2[c:18]1[O:19][CH2:20][CH:21]2[c:22]1[cH:23][cH:24][c:25]([CH:26]([CH3:27])[CH3:28])[cH:29][cH:30]1>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]([NH:7][C:8](=[O:9])[CH2:10][C:11]([CH3:12])([CH3:13... | CCOC(C)=O.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2 | COc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | null | [Cu]Br | C[O-].[Na+].CO | Heteroatom Alkylation and Arylation | OtherReaction | d6498ace3fd4b04fcd053b8f11cca1308ae891716caacafdfea7563f75659df2 | 5c46ebc63b29f5e7138723258aaaa965349a056969ed2898b01eaa65c7960fb8 | c1ccc(C2COc3ccccc32)cc1 | Br-[c;H0;D3;+0:1](:[c:2](:[c:3])-[#8:4]-[C:5]):[c:6](-[C;D1;H3:7]):[c:8].C-C-O-[C;H0;D3;+0:9](-C)=[O;H0;D1;+0:10]>>[C:5]-[#8:4]-[c:2](:[c:3]):[c;H0;D3;+0:1](-[O;H0;D2;+0:10]-[CH3;D1;+0:9]):[c:6](-[C;D1;H3:7]):[c:8] | 58.2 | [{"value": 58.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2OC)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.2, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2OC)C)NC(CC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of N-(7-bromo-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (250 mg, 0.545 mmol) obtained in Example 35, copper(I) bromide (78 mg, 0.545 mmol), ethyl acetate (88 mg, 1.00 mmol), and 28% sodium methoxide-methanol solution (20 mL) was refluxed with heating for 6 hours.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester | Ether | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | HBr | [Cu]Br.C[O-].[Na+].CO | null | null | CCOC(C)=O.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)C(c1ccc(C(C)C)cc1)CO2>[Cu]Br.C[O-].[Na+].CO>COc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-34d8a8d328e844418488009b05d12120 | CCCCCC.CCOC(C)=O.Cc1cc2c(c(C)c1N)[C@@H](c1ccc(C(C)C)cc1)CO2>>Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2 | C(C)(C)C1=CC=C(C=C1)[C@H]1COC2=C1C(=C(C(=C2)C)N)C.C(C)(=O)OCC.CCCCCC.C(Cl)(Cl)Cl>>C(C)(C)C1=CC=C(C=C1)[C@H]1COC2=C1C(=C(C(=C2)C)NC(CC(C)(C)C)=O)C | CC[CH2:15][CH2:16][CH2:13][CH3:14].CCO[C:10](=[O:11])[CH3:12].[CH3:1][c:2]1[cH:3][c:4]2[c:5]([c:6]([CH3:7])[c:8]1[NH2:9])[C@@H:17]([c:18]1[cH:19][cH:20][c:21]([CH:22]([CH3:23])[CH3:24])[cH:25][cH:26]1)[CH2:27][O:28]2>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([c:6]([CH3:7])[c:8]1[NH:9][C:10](=[O:11])[CH2:12][C:13]([CH3:14])([CH3:... | CCCCCC.CCOC(C)=O.Cc1cc2c(c(C)c1N)[C@@H](c1ccc(C(C)C)cc1)CO2 | Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2 | null | null | null | Acylation | OtherReaction | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1ccc([C@H]2COc3ccccc32)cc1 | C-C-O-[C;H0;D3;+0:1](-[CH3;D1;+0:2])=[O;D1;H0:3].C-C-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[C;D1;H3:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:7]-[C;H0;D4;+0:6](-[CH3;D1;+0:4])(-[CH3;D1;+0:5])-[CH2;D2;+0:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 93 | [{"value": 93.0, "product": "C(C)(C)C1=CC=C(C=C1)[C@H]1COC2=C1C(=C(C(=C2)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using (+)-(3R)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-amine obtained in Reference Example 141, the title compound was synthesized in the same manner as in Example 1. Yield: 93%. Melting point: 148-149° C. (ethyl acetate-hexane). [α]D20=+93.2° (c=0.54, chloroform).
Conditions: See reaction.notes.p... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | HO- | null | null | null | CCCCCC.CCOC(C)=O.Cc1cc2c(c(C)c1N)[C@@H](c1ccc(C(C)C)cc1)CO2>>Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d703721fb8bf4a8990114f0c8463ad78 | CC(=O)Cl.Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2>>CC(=O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OC[C@@H]2c1ccc(C(C)C)cc1 | C(C)(=O)Cl.C(C)(C)C1=CC=C(C=C1)[C@H]1COC2=C1C(=C(C(=C2)C)NC(CC(C)(C)C)=O)C.[Cl-].[Al+3].[Cl-].[Cl-]>>C(C)(=O)C1=C(C(=C(C=2[C@H](COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | Cl[C:2]([CH3:1])=[O:3].[cH:4]1[c:5]([CH3:6])[c:7]([NH:8][C:9](=[O:10])[CH2:11][C:12]([CH3:13])([CH3:14])[CH3:15])[c:16]([CH3:17])[c:18]2[c:19]1[O:20][CH2:21][C@@H:22]2[c:23]1[cH:24][cH:25][c:26]([CH:27]([CH3:28])[CH3:29])[cH:30][cH:31]1>>[CH3:1][C:2](=[O:3])[c:4]1[c:5]([CH3:6])[c:7]([NH:8][C:9](=[O:10])[CH2:11][C:12]([... | CC(=O)Cl.Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2 | CC(=O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OC[C@@H]2c1ccc(C(C)C)cc1 | null | null | ClCCl | C-C Coupling | Friedel-Crafts acylation | f8d339b78f15a4d82452b51f6749e04de87b23cf8586247567d903b7cafd77bf | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1ccc([C@H]2COc3ccccc32)cc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[#8:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9](-[C;D1;H3:10]):[c:11]>>[C:4]-[#8:5]-[c:6](:[c:7]):[c;H0;D3;+0:8](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]):[c:9](-[C;D1;H3:10]):[c:11] | 84.2 | [{"value": 84.0, "product": "C(C)(=O)C1=C(C(=C(C=2[C@H](COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.2, "product": "C(C)(=O)C1=C(C(=C(C=2[C@H](COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 10 | CELSIUS | 20 | MINUTE | To a solution of (+)-N-((3R)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (933 mg, 2.46 mmol) obtained in Example 37 in dichloromethane (20 mL) was added aluminum chloride (721 mg, 5.40 mmol) at −70° C. under an argon atmosphere and the mixture was stirred for 20 minutes. To ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | HCl | ClCCl | 10 | 0.333333 | CC(=O)Cl.Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2>ClCCl>CC(=O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OC[C@@H]2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-24e9c6fbbc9142a58b70a03c3884815c | CCOC(C)=O.Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2>>Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2 | C(C)(C)C1=CC=C(C=C1)[C@H]1COC2=C1C(=C(C(=C2)C)NC(CC(C)(C)C)=O)C.C(C)(=O)OCC.CCCCCC>>C(=O)C1=C(C(=C(C=2[C@H](COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | CCO[C:4](C)=[O:5].[CH3:1][c:2]1[cH:3][c:6]2[c:7]([c:8]([CH3:9])[c:10]1[NH:11][C:12](=[O:13])[CH2:14][C:15]([CH3:16])([CH3:17])[CH3:18])[C@@H:19]([c:20]1[cH:21][cH:22][c:23]([CH:24]([CH3:25])[CH3:26])[cH:27][cH:28]1)[CH2:29][O:30]2>>[CH3:1][c:2]1[c:3]([CH:4]=[O:5])[c:6]2[c:7]([c:8]([CH3:9])[c:10]1[NH:11][C:12](=[O:13])[... | CCOC(C)=O.Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2 | Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2 | null | null | C(Cl)(Cl)Cl | C-C Coupling | OtherReaction | 2ca0c0d3b49721488f46a629c9ef66812e09f5949b927e1102590183256d1725 | 77724e9f3c3ba29a4aa00a2bd379f1beb2d911c11d7760b291574be7e0156860 | c1ccc([C@H]2COc3ccccc32)cc1 | C-C-O-[C;H0;D3;+0:1](-C)=[O;D1;H0:2].[C:3]-[#8:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8](-[C;D1;H3:9]):[c:10]>>[C:3]-[#8:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[CH;D2;+0:1]=[O;D1;H0:2]):[c:8](-[C;D1;H3:9]):[c:10] | 83 | [{"value": 83.0, "product": "C(=O)C1=C(C(=C(C=2[C@H](COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using (+)-N-((3R)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 37, the title compound was synthesized in the same manner as in Example 20. Yield: 83%. Melting point: 179-180° C. (ethyl acetate-hexane). [α]D20=−25.8° (c=0.48, chloroform).
Conditions: See re... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aldehyde | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | HO- | C(Cl)(Cl)Cl | null | null | CCOC(C)=O.Cc1cc2c(c(C)c1NC(=O)CC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2>C(Cl)(Cl)Cl>Cc1c(C=O)c2c(c(C)c1NC(=O)CC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-427b11d22ec0464585b0f2f7055fd823 | CCC(O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OC[C@@H]2c1ccc(C(C)C)cc1>>CCCc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OC[C@@H]2c1ccc(C(C)C)cc1 | OC(CC)C1=C(C(=C(C=2[C@H](COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C>>C(C)(C)C1=CC=C(C=C1)[C@H]1COC2=C1C(=C(C(=C2CCC)C)NC(CC(C)(C)C)=O)C | O[CH:3]([CH2:2][CH3:1])[c:4]1[c:5]([CH3:6])[c:7]([NH:8][C:9](=[O:10])[CH2:11][C:12]([CH3:13])([CH3:14])[CH3:15])[c:16]([CH3:17])[c:18]2[c:19]1[O:20][CH2:21][C@@H:22]2[c:23]1[cH:24][cH:25][c:26]([CH:27]([CH3:28])[CH3:29])[cH:30][cH:31]1>>[CH3:1][CH2:2][CH2:3][c:4]1[c:5]([CH3:6])[c:7]([NH:8][C:9](=[O:10])[CH2:11][C:12]([... | CCC(O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OC[C@@H]2c1ccc(C(C)C)cc1 | CCCc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OC[C@@H]2c1ccc(C(C)C)cc1 | null | [Pd] | C(C)(=O)O | Reduction | OtherReaction | 3c5af32aa639db2ebe4d9851942e9468e1838e06ae5b2c1669bca1d5e0922c33 | 46f8a11b80b06e754a5a34198d843342612a5e7ede950bda52ce3a500cedba0b | c1ccc([C@H]2COc3ccccc32)cc1 | O-[CH;D3;+0:1](-[C:2]-[C;D1;H3:3])-[c:4](:[c:5]):[c:6]-[#8:7]>>[#8:7]-[c:6]:[c:4](-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3]):[c:5] | 71 | [{"value": 71.0, "product": "C(C)(C)C1=CC=C(C=C1)[C@H]1COC2=C1C(=C(C(=C2CCC)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.7, "product": "C(C)(C)C1=CC=C(C=C1)[C@H]1COC2=C1C(=C(C(=C2CCC)C)NC(CC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of a diastereo mixture of (+)-N-((3R)-7-(1-hydroxypropyl)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (620 mg, 1.42 mmol) obtained in Examples 43 and 44, and 10% palladium on carbon (water content: 50%, 62 mg) in acetic acid (3 mL) was reacted at 80° C. for 2 hour... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | null | null | c1ccc2c(c1)CCO2.c1ccccc1 | Other | [Pd].C(C)(=O)O | null | null | CCC(O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OC[C@@H]2c1ccc(C(C)C)cc1>[Pd].C(C)(=O)O>CCCc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OC[C@@H]2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-19d96c5925f642f69271214d99035430 | CC(=O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OC[C@@H]2c1ccc(C(C)C)cc1.CCCCCC>>Cc1c(NC(=O)CC(C)(C)C)c(C)c(C(C)(C)O)c2c1[C@@H](c1ccc(C(C)C)cc1)CO2 | C(C)(=O)C1=C(C(=C(C=2[C@H](COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.C(C)(=O)OCC.CCCCCC>>OC(C)(C)C1=C(C(=C(C=2[C@H](COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C | [CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[CH3:11])[c:12]([CH3:13])[c:14]([C:15]([CH3:16])=[O:18])[c:19]2[c:20]1[C@@H:21]([c:22]1[cH:23][cH:24][c:25]([CH:26]([CH3:27])[CH3:28])[cH:29][cH:30]1)[CH2:31][O:32]2.CCCCC[CH3:17]>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[... | CC(=O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OC[C@@H]2c1ccc(C(C)C)cc1.CCCCCC | Cc1c(NC(=O)CC(C)(C)C)c(C)c(C(C)(C)O)c2c1[C@@H](c1ccc(C(C)C)cc1)CO2 | null | null | C(Cl)(Cl)Cl | C-C Coupling | OtherReaction | 2fffd6bd6bacb879d7ba2cf29351570d50899c51664d6359aa6c9ef1859cb5dd | 454f67ba8644982dc9f605915a0f36178771eadaffb50d3f1e0f17f2b6fdeb10 | c1ccc([C@H]2COc3ccccc32)cc1 | C-C-C-C-C-[CH3;D1;+0:1].[#8:2]-[c:3]:[c:4](-[C;H0;D3;+0:5](-[C;D1;H3:6])=[O;H0;D1;+0:7]):[c:8]>>[#8:2]-[c:3]:[c:4](-[C;H0;D4;+0:5](-[C;D1;H3:6])(-[CH3;D1;+0:1])-[OH;D1;+0:7]):[c:8] | 82 | [{"value": 82.0, "product": "OC(C)(C)C1=C(C(=C(C=2[C@H](COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using (+)-N-((3R)-7-acetyl-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 38, the title compound was synthesized in the same manner as in Example 22. Yield: 82%. Melting point: 141-142° C. (ethyl acetate-hexane). [α]D20+40.8° (c=0.46, chloroform).
Conditions... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | Other | C(Cl)(Cl)Cl | null | null | CC(=O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OC[C@@H]2c1ccc(C(C)C)cc1.CCCCCC>C(Cl)(Cl)Cl>Cc1c(NC(=O)CC(C)(C)C)c(C)c(C(C)(C)O)c2c1[C@@H](c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-43cfa6aa134042849aa6ab81d1e86173 | CC(C)(C)N.Cc1cc2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2>>Cc1cc2c(c(C)c1NC(=O)NC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2 | ClC(=O)OCC(Cl)(Cl)Cl.C(C)N(CC)CC.C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2)C)NC(OCC(Cl)(Cl)Cl)=O)C.C(C)(C)(C)N>>C(C)(C)(C)NC(=O)NC=1C(=CC2=C([C@H](CO2)C2=CC=C(C=C2)C(C)C)C1C)C | [NH2:12][C:13]([CH3:14])([CH3:15])[CH3:16].ClC(Cl)(Cl)CO[C:10]([NH:9][c:8]1[c:2]([CH3:1])[cH:3][c:4]2[c:5]([c:6]1[CH3:7])[CH:17]([c:18]1[cH:19][cH:20][c:21]([CH:22]([CH3:23])[CH3:24])[cH:25][cH:26]1)[CH2:27][O:28]2)=[O:11]>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([c:6]([CH3:7])[c:8]1[NH:9][C:10](=[O:11])[NH:12][C:13]([CH3:14])(... | CC(C)(C)N.Cc1cc2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2 | Cc1cc2c(c(C)c1NC(=O)NC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2 | null | null | O.CS(=O)C | Acylation | OtherReaction | 08db0e358f3e3681babcf09515305cf765cd40aaf4e5eb7c0833c23986da21d7 | a25721dc05afcaa855a5cf6497abad03f925cbf14d4240249ec4feb62b1990eb | c1ccc([C@H]2COc3ccccc32)cc1 | Cl-C(-Cl)(-Cl)-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4].[C;D1;H3:5]-[C:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[NH2;D1;+0:9]>>[C;D1;H3:5]-[C:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[c:4] | 89.4 | [{"value": 88.0, "product": "C(C)(C)(C)NC(=O)NC=1C(=CC2=C([C@H](CO2)C2=CC=C(C=C2)C(C)C)C1C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.4, "product": "C(C)(C)(C)NC(=O)NC=1C(=CC2=C([C@H](CO2)C2=CC=C(C=C2)C(C)C)C1C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of (+)-(3R)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-amine (1.0 g, 3.55 mmol) obtained in Reference Example 141 in THF (10 mL) was added dropwise with ice-cooling 2,2,2-trichloroethyl chloroformate (0.49 mL, 3.55 mmol), was added triethylamine (0.52 mL, 3.73 mmol) and the reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Carbamic ester.Ether.Primary amine | Urea | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | HCl | O.CS(=O)C | null | 0.5 | CC(C)(C)N.Cc1cc2c(c(C)c1NC(=O)OCC(Cl)(Cl)Cl)C(c1ccc(C(C)C)cc1)CO2>O.CS(=O)C>Cc1cc2c(c(C)c1NC(=O)NC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-abe2a1165afd4a07b0f80d4a45a490bb | CCOC(C)=O.Cc1cc2c(c(C)c1NC(=O)NC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2>>Cc1c(C=O)c2c(c(C)c1NC(=O)NC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2 | C(C)(C)(C)NC(=O)NC=1C(=CC2=C([C@H](CO2)C2=CC=C(C=C2)C(C)C)C1C)C.C(C)(=O)OCC.CCCCCC>>C(C)(C)(C)NC(=O)NC=1C(=C(C2=C([C@H](CO2)C2=CC=C(C=C2)C(C)C)C1C)C=O)C | CCO[C:4](C)=[O:5].[CH3:1][c:2]1[cH:3][c:6]2[c:7]([c:8]([CH3:9])[c:10]1[NH:11][C:12](=[O:13])[NH:14][C:15]([CH3:16])([CH3:17])[CH3:18])[C@@H:19]([c:20]1[cH:21][cH:22][c:23]([CH:24]([CH3:25])[CH3:26])[cH:27][cH:28]1)[CH2:29][O:30]2>>[CH3:1][c:2]1[c:3]([CH:4]=[O:5])[c:6]2[c:7]([c:8]([CH3:9])[c:10]1[NH:11][C:12](=[O:13])[N... | CCOC(C)=O.Cc1cc2c(c(C)c1NC(=O)NC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2 | Cc1c(C=O)c2c(c(C)c1NC(=O)NC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2 | null | null | C(Cl)(Cl)Cl | C-C Coupling | OtherReaction | 2ca0c0d3b49721488f46a629c9ef66812e09f5949b927e1102590183256d1725 | 77724e9f3c3ba29a4aa00a2bd379f1beb2d911c11d7760b291574be7e0156860 | c1ccc([C@H]2COc3ccccc32)cc1 | C-C-O-[C;H0;D3;+0:1](-C)=[O;D1;H0:2].[C:3]-[#8:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8](-[C;D1;H3:9]):[c:10]>>[C:3]-[#8:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[CH;D2;+0:1]=[O;D1;H0:2]):[c:8](-[C;D1;H3:9]):[c:10] | 78 | [{"value": 78.0, "product": "C(C)(C)(C)NC(=O)NC=1C(=C(C2=C([C@H](CO2)C2=CC=C(C=C2)C(C)C)C1C)C=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using (+)-N-(tert-butyl)-N′-((3R)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)urea, the title compound was synthesized in the same manner as in Example 20. Yield: 78%. Melting point: 209-210° C. (ethyl acetate-hexane). [α]D20=−31.2° (c=0.48, chloroform).
Conditions: See reaction.notes.procedure_det... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aldehyde | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | HO- | C(Cl)(Cl)Cl | null | null | CCOC(C)=O.Cc1cc2c(c(C)c1NC(=O)NC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2>C(Cl)(Cl)Cl>Cc1c(C=O)c2c(c(C)c1NC(=O)NC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7db3b81da5984279a05942288290e08e | Cc1c(C=O)c2c(c(C)c1NC(=O)NC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2>>Cc1c(CO)c2c(c(C)c1NC(=O)NC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2 | C(C)(C)(C)NC(=O)NC=1C(=C(C2=C([C@H](CO2)C2=CC=C(C=C2)C(C)C)C1C)C=O)C.C(C)(=O)OCC.CCCCCC>>C(C)(C)(C)NC(=O)NC=1C(=C(C2=C([C@H](CO2)C2=CC=C(C=C2)C(C)C)C1C)CO)C | [CH3:1][c:2]1[c:3]([CH:4]=[O:5])[c:6]2[c:7]([c:8]([CH3:9])[c:10]1[NH:11][C:12](=[O:13])[NH:14][C:15]([CH3:16])([CH3:17])[CH3:18])[C@@H:19]([c:20]1[cH:21][cH:22][c:23]([CH:24]([CH3:25])[CH3:26])[cH:27][cH:28]1)[CH2:29][O:30]2>>[CH3:1][c:2]1[c:3]([CH2:4][OH:5])[c:6]2[c:7]([c:8]([CH3:9])[c:10]1[NH:11][C:12](=[O:13])[NH:14... | Cc1c(C=O)c2c(c(C)c1NC(=O)NC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2 | Cc1c(CO)c2c(c(C)c1NC(=O)NC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2 | null | null | C(Cl)(Cl)Cl | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccc([C@H]2COc3ccccc32)cc1 | [#8:1]-[c:2]:[c:3](-[CH;D2;+0:4]=[O;H0;D1;+0:5]):[c:6]>>[#8:1]-[c:2]:[c:3](-[CH2;D2;+0:4]-[OH;D1;+0:5]):[c:6] | 97 | [{"value": 97.0, "product": "C(C)(C)(C)NC(=O)NC=1C(=C(C2=C([C@H](CO2)C2=CC=C(C=C2)C(C)C)C1C)CO)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using (−)-N-(tert-butyl)-N′-((3R)-7-formyl-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)urea obtained in Example 48, the title compound was synthesized in the same manner as in Example 21. Yield: 97%. Melting point: 187-188° C. (ethyl acetate-hexane). [α]D20+34.0° (c=0.43, chloroform).
Conditions: S... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | null | C(Cl)(Cl)Cl | null | null | Cc1c(C=O)c2c(c(C)c1NC(=O)NC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2>C(Cl)(Cl)Cl>Cc1c(CO)c2c(c(C)c1NC(=O)NC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cbeb70e0431a454dbd83394698d3902a | Cc1c(CO)c2c(c(C)c1NC(=O)NC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2>>Cc1c(C)c2c(c(C)c1NC(=O)NC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2 | C(C)(C)(C)NC(=O)NC=1C(=C(C2=C([C@H](CO2)C2=CC=C(C=C2)C(C)C)C1C)CO)C.C(C)(=O)OCC.CCCCCC>>C(C)(C)(C)NC(=O)NC=1C(=C(C2=C([C@H](CO2)C2=CC=C(C=C2)C(C)C)C1C)C)C | O[CH2:4][c:3]1[c:2]([CH3:1])[c:9]([NH:10][C:11](=[O:12])[NH:13][C:14]([CH3:15])([CH3:16])[CH3:17])[c:7]([CH3:8])[c:6]2[c:5]1[O:29][CH2:28][C@@H:18]2[c:19]1[cH:20][cH:21][c:22]([CH:23]([CH3:24])[CH3:25])[cH:26][cH:27]1>>[CH3:1][c:2]1[c:3]([CH3:4])[c:5]2[c:6]([c:7]([CH3:8])[c:9]1[NH:10][C:11](=[O:12])[NH:13][C:14]([CH3:1... | Cc1c(CO)c2c(c(C)c1NC(=O)NC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2 | Cc1c(C)c2c(c(C)c1NC(=O)NC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2 | null | null | C(Cl)(Cl)Cl | Reduction | OtherReaction | 1deafbccd34c1d747dea179c0b63e48cd7fc76936d377fecabe099ecef578991 | 0a2c8330040d049ae67653e1474aff520bf8a2d8c908ffd7076f536576936945 | c1ccc([C@H]2COc3ccccc32)cc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-[#8:5]>>[#8:5]-[c:4]:[c:2](-[CH3;D1;+0:1]):[c:3] | 57 | [{"value": 57.0, "product": "C(C)(C)(C)NC(=O)NC=1C(=C(C2=C([C@H](CO2)C2=CC=C(C=C2)C(C)C)C1C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using (+)-N-(tert-butyl)-N′-((3R)-7-(hydroxymethyl)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)urea obtained in Example 49, the title compound was synthesized in the same manner as in Example 45. Yield: 57%. Melting point: 209-210° C. (ethyl acetate-hexane). [α]D20=+53.2° (c=0.47, chloroform).
Con... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | null | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | Other | C(Cl)(Cl)Cl | null | null | Cc1c(CO)c2c(c(C)c1NC(=O)NC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2>C(Cl)(Cl)Cl>Cc1c(C)c2c(c(C)c1NC(=O)NC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-afa77f0a4613425baa5fbcd47477deff | CCOC(C)=O.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2>>COc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OC[C@@H]2c1ccc(C(C)C)cc1 | BrC1=C(C(=C(C=2[C@H](COC21)C2=CC=C(C=C2)C(C)C)C)NC(CC(C)(C)C)=O)C.C(C)(=O)OCC.CCCCCC>>C(C)(C)C1=CC=C(C=C1)[C@H]1COC2=C1C(=C(C(=C2OC)C)NC(CC(C)(C)C)=O)C | CCO[C:1](C)=[O:2].Br[c:3]1[c:4]([CH3:5])[c:6]([NH:7][C:8](=[O:9])[CH2:10][C:11]([CH3:12])([CH3:13])[CH3:14])[c:15]([CH3:16])[c:17]2[c:18]1[O:19][CH2:20][C@@H:21]2[c:22]1[cH:23][cH:24][c:25]([CH:26]([CH3:27])[CH3:28])[cH:29][cH:30]1>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]([NH:7][C:8](=[O:9])[CH2:10][C:11]([CH3:12])([CH3:... | CCOC(C)=O.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2 | COc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OC[C@@H]2c1ccc(C(C)C)cc1 | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | d6498ace3fd4b04fcd053b8f11cca1308ae891716caacafdfea7563f75659df2 | 5c46ebc63b29f5e7138723258aaaa965349a056969ed2898b01eaa65c7960fb8 | c1ccc([C@H]2COc3ccccc32)cc1 | Br-[c;H0;D3;+0:1](:[c:2](:[c:3])-[#8:4]-[C:5]):[c:6](-[C;D1;H3:7]):[c:8].C-C-O-[C;H0;D3;+0:9](-C)=[O;H0;D1;+0:10]>>[C:5]-[#8:4]-[c:2](:[c:3]):[c;H0;D3;+0:1](-[O;H0;D2;+0:10]-[CH3;D1;+0:9]):[c:6](-[C;D1;H3:7]):[c:8] | 98 | [{"value": 98.0, "product": "C(C)(C)C1=CC=C(C=C1)[C@H]1COC2=C1C(=C(C(=C2OC)C)NC(CC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using (−)-N-((3R)-7-bromo-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 51, the title compound was synthesized in the same manner as in Example 36. Yield: 98%. Melting point: 150-151° C. (ethyl acetate-hexane). [α]D20=+55.9° (c=0.50, chloroform).
Conditions... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester | Ether | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2.c1ccccc1 | HBr | C(Cl)(Cl)Cl | null | null | CCOC(C)=O.Cc1c(Br)c2c(c(C)c1NC(=O)CC(C)(C)C)[C@@H](c1ccc(C(C)C)cc1)CO2>C(Cl)(Cl)Cl>COc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OC[C@@H]2c1ccc(C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b096e555ad7d4002990d57520cfcad9e | CCOC(C)=O.Cc1cc2c(c(C)c1N)C(c1ccc(C(C)C)cc1)CO2>>Cc1cc2c(c(C)c1NC=O)C(c1ccc(C(C)C)cc1)CO2 | C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2)C)N)C.CCCCCC.C(C)(=O)OCC>>C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2)C)NC=O)C | CCO[C:10](C)=[O:11].[CH3:1][c:2]1[cH:3][c:4]2[c:5]([c:6]([CH3:7])[c:8]1[NH2:9])[CH:12]([c:13]1[cH:14][cH:15][c:16]([CH:17]([CH3:18])[CH3:19])[cH:20][cH:21]1)[CH2:22][O:23]2>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([c:6]([CH3:7])[c:8]1[NH:9][CH:10]=[O:11])[CH:12]([c:13]1[cH:14][cH:15][c:16]([CH:17]([CH3:18])[CH3:19])[cH:20][cH:2... | CCOC(C)=O.Cc1cc2c(c(C)c1N)C(c1ccc(C(C)C)cc1)CO2 | Cc1cc2c(c(C)c1NC=O)C(c1ccc(C(C)C)cc1)CO2 | null | null | null | Acylation | OtherReaction | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1ccc(C2COc3ccccc32)cc1 | C-C-O-[C;H0;D3;+0:1](-C)=[O;D1;H0:2].[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[O;D1;H0:2]=[CH;D2;+0:1]-[NH;D2;+0:3]-[c:4](:[c:5]):[c:6] | 81 | [{"value": 81.0, "product": "C(C)(C)C1=CC=C(C=C1)C1COC2=C1C(=C(C(=C2)C)NC=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using 3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-amine obtained in Reference Example 32, the title compound was synthesized in the same manner as in Reference Example 73. Yield: 81%. Melting point: 193-196° C. (hexane-ethyl acetate).
Conditions: See reaction.notes.procedure_details.
Workup: obtained ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)CCO2 | HO- | null | null | null | CCOC(C)=O.Cc1cc2c(c(C)c1N)C(c1ccc(C(C)C)cc1)CO2>>Cc1cc2c(c(C)c1NC=O)C(c1ccc(C(C)C)cc1)CO2 |
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