3-Cyclopentyl-2-(4-nitro-phenyl)-propionic acid ethyl ester → 2-(4-Amino-phenyl)-3-cyclopentyl-propionic acid ethyl ester

HRID 1935290Notes

Reaction equation

HRID 1935290 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH:5]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1)[CH2:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)[CH3:2].[H][H]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:21])[CH:5]([C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=1)[CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1)[CH3:2]

Participants

5

Reactant 2

HCID 114718493-Cyclopentyl-2-(4-nitro-phenyl)-propionic acid ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 541707732-(4-Amino-phenyl)-3-cyclopentyl-propionic acid ethyl esterYield 53.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-cyclopentyl-2-(4-nitro-phenyl)-propionic acid ethyl ester (7.37 g, 25.3 mmol) in ethyl acetate (316 mL) was treated with 10% palladium on activated carbon (500 g). The reaction mixture was shaken under 60 psi of hydrogen gas at 25° C. for 18 h. The catalyst was then filtered off through a pad of celite and was washed with ethyl acetate. The filtrate was concentrated in vacuo to give 2-(4-amino-phenyl)-3-cyclopentyl-propionic acid ethyl ester (3.52 g, 53.3%) as a yellow oil: EI-HRMS m/e calcd for C16H23NO2 (M+) 261.1727, found 261.1727.

Workup

  1. filtrationThe catalyst was then filtered off through a pad of celite
  2. washwas washed with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-fef456d5db8441c79cbf1e864b0a9da7
Source dataset
uspto-grants-2002_05
Patent number
US06384220B2

Reaction notes

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