Ethyl 1-(4-nitro-3-(2,2,2-trifluoroethoxy)phenyl)cyclopentane carboxylate → Ethyl 1-(4-amino-3-(2,2,2-trifluoroethoxy)phenyl)cyclopentanecarboxylate

HRID 1512486Notes

Reaction equation

HRID 1512486 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:6][C:5]=1[O:20][CH2:21][C:22]([F:25])([F:24])[F:23])([O-])=O>CO>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:6][C:5]=1[O:20][CH2:21][C:22]([F:23])([F:24])[F:25]

Participants

3

Reactant 1

HCID 57995644Ethyl 1-(4-nitro-3-(2,2,2-trifluoroethoxy)phenyl)cyclopentane carboxylate

Product 1

HCID 57995594Ethyl 1-(4-amino-3-(2,2,2-trifluoroethoxy)phenyl)cyclopentanecarboxylateYield 81.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of ethyl 1-(4-nitro-3-(2,2,2-trifluoroethoxy)phenyl)cyclopentane carboxylate (10 g), in dry MeOH (100 mL) Pd(OH)2 (2 g) was added and reduced under an atmosphere of H2 for 6 h at room temperature. The mixture was filtered through a pad of Celite™ washing with MeOH. The combined filtrates were concentrated under reduced pressure to yield ethyl 1-(4-amino-3-(2,2,2-trifluoroethoxy)phenyl)cyclopentanecarboxylate (7.5 g ) as a thick liquid.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite™
  2. washwashing with MeOH
  3. concentrationThe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-26840b7bf18a4366ae7c70d0cf03bdf1
Source dataset
uspto-grants-2012_07
Patent number
US08217064B2

Reaction notes

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