3-Cyclopentyl-2-(4-nitrophenyl)propionic acid → HCID 11436223, compound

HRID 2296947Notes

Reaction equation

HRID 2296947 reaction equation
[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)[C:8]([OH:10])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>C(OCC)(=O)C.[Pd]>[NH2:17][C:14]1[CH:13]=[CH:12][C:11]([CH:7]([CH2:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[C:8]([OH:10])=[O:9])=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 117371213-Cyclopentyl-2-(4-nitrophenyl)propionic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 11436223HCID 11436223, compoundYield 135.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-cyclopentyl-2-(4-nitro-phenyl)-propionic acid (100 mg, 0.38 mmol) in ethyl acetate (50 mL) was treated with 10% palladium on activated carbon. The reaction mixture was stirred under 60 psi of hydrogen gas at 25° C. for 16 h. The catalyst was removed by filtration through a pad of celite and was washed with ethyl acetate. The filtrate was concentrated in vacuo to afford 2-(4-amino-phenyl)-3-cyclopentyl-propionic acid (120 mg, 100%) as a white solid: mp 167-169° C.; EI-HRMS m/e calcd for C14H19NO2 (M+) 233.1415, found 233.1413.

Workup

  1. customThe catalyst was removed by filtration through a pad of celite
  2. washwas washed with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-5deb40bcfae14a699dd055d05248e10c
Source dataset
uspto-grants-2002_12
Patent number
US06489485B2

Reaction notes

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