Ethyl 2-(3-(4-aminophenyl)cyclohexyl)acetate → Ethyl [(3S)-3-(4-aminophenyl)cyclopentylidene]acetate

HRID 1713853Notes

Reaction equation

HRID 1713853 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12]C[CH:10]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:9]2)=[CH:4][CH:3]=1.C1(C(=NC2C=CC([C@H]3CCC(=CC(OCC)=O)C3)=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[CH2:13][CH2:12][C:10](=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:9]2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 59464273Ethyl 2-(3-(4-aminophenyl)cyclohexyl)acetate2×HCID 86619817ethyl ((3S)-3-{4-[(diphenylmethylene)amino]phenyl}cyclopentylidene)acetate

Product 1

HCID 86619816Ethyl [(3S)-3-(4-aminophenyl)cyclopentylidene]acetate

Procedure

Following the procedure described for ethyl [3-(4-aminophenyl)cyclohexyl]acetate (Intermediate 89(iv)), replacing ethyl (3-{4-[(diphenylmethylene)amino]phenyl}cyclohexyl)acetate with ethyl ((3S)-3-{4-[(diphenylmethylene)amino]phenyl}cyclopentylidene)acetate the title compound was obtained; 1H NMR δ 1.17-1.22 (3H, m), 1.57-1.68 (1H, m), 2.27-2.48 (2H, m), 2.53 (OH, s), 2.56-2.68 (1H, m), 2.74-2.76 (1H, m), 2.93-3.00 (1H, m), 3.15-3.24 (0.5H, m), 3.69-3.71 (0.5H, m), 4.01-4.12 (2H, m), 4.79-4.83 (2H, m), 5.49-5.53 (1H, m), 5.78-5.82 (1H, m), 6.47-6.52 (2H, m), 6.80-6.93 (2H, m); MS m/e M+MeCN 287.

Sources & evidence

ORD record
ord-250650d388a948f889d08ecffaec5537
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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