Methyl 3-(4-nitrophenyl)cyclopentanecarboxylate → Ethyl [(3S)-3-(4-aminophenyl)cyclopentyl]acetate

HRID 1713854Notes

Reaction equation

HRID 1713854 reaction equation
NC1C=CC(C2CCC(C(OC)=O)C2)=CC=1.[N+](C1C=CC(C2CCC(C(OC)=O)C2)=CC=1)([O-])=O.[NH2:35][C:36]1[CH:41]=[CH:40][C:39]([C@H:42]2[CH2:46][CH2:45][C:44](=[CH:47][C:48]([O:50][CH2:51][CH3:52])=[O:49])[CH2:43]2)=[CH:38][CH:37]=1>>[NH2:35][C:36]1[CH:37]=[CH:38][C:39]([C@H:42]2[CH2:46][CH2:45][CH:44]([CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49])[CH2:43]2)=[CH:40][CH:41]=1

Participants

4

Reactant 3

HCID 59464325Methyl 3-(4-nitrophenyl)cyclopentanecarboxylateHCID 59464327Methyl 3-(4-aminophenyl)cyclopentanecarboxylateHCID 86619816Ethyl [(3S)-3-(4-aminophenyl)cyclopentylidene]acetate

Product 1

HCID 59619573Ethyl [(3S)-3-(4-aminophenyl)cyclopentyl]acetate

Procedure

Following the procedure described for methyl 3-(4-aminophenyl)cyclopentanecarboxylate, replacing methyl 3-(4-nitrophenyl)cyclopentanecarboxylate (Intermediate 84(ii)) with ethyl [(3S)-3-(4-aminophenyl)cyclopentylidene]acetate the title compound was obtained; 1H NMR δ1.18 (t, 3H), 1.21-1.76 (m, 2H), 1.80-2.12 (m, 2H), 2.23-2.48 (m, 2H), 2.80-3.01 (m, 1H), 3.16-3.30 (m, 2H), 4.06 (q, 2H), 4.79 (s, 2H), 6.45-6.51 (m, 2H), 6.84-6.91 (m, 2H); MS m/e M+MeCN 289.

Sources & evidence

ORD record
ord-59ea40be5fd348f79b7531aa0a143dc8
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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