HCID 68715913, compound → 3,3-Difluorocyclopentane-1-carboxylic acid

HRID 920808Notes

Reaction equation

HRID 920808 reaction equation
[F:1][C:2]1([F:17])[CH2:6][CH2:5][CH:4]([C:7]([O:9]CC2C=CC=CC=2)=[O:8])[CH2:3]1>CCOC(C)=O.[Pd]>[F:1][C:2]1([F:17])[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3]1

Participants

4

Reactant 1

HCID 68715913HCID 68715913, compound

Product 1

HCID 534038373,3-Difluorocyclopentane-1-carboxylic acidYield 80.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of Intermediate 332B (0.07 g, 0.291 mmol) in EtOAc (2 mL) was added 10% Pd/C (0.016 g, 0.015 mmol) and the resulting mixture was stirred for 16 h under an atmosphere of hydrogen (15 psi, balloon pressure). The reaction mixture was filtered through a pad of CELITE® and the filter cake was washed with EtOAc. The combined filtrate was concentrated under reduced pressure to afford Intermediate 332C as a colorless oil (0.035 g, 76% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.41 (br. s., 1H), 3.04-2.94 (m, 1H), 2.39-2.23 (m, 2H), 2.20-2.01 (m, 3H), 1.95-1.84 (m, 1H).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of CELITE®
  2. washthe filter cake was washed with EtOAc
  3. concentrationThe combined filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e8acacd8f6bb49fab0973a4f6f1a15e0
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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