HCID 86690096, compound → 3,3-Difluorocyclopentane-1-carboxylic acid

HRID 520380Notes

Reaction equation

HRID 520380 reaction equation
[F:1][C:2]1([F:18])[CH2:6][CH2:5][CH:4]([C:7]([O:9][C@H](C2C=CC=CC=2)C)=[O:8])[CH2:3]1>C(O)C.[Pd]>[F:1][C:2]1([F:18])[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3]1

Participants

4

Reactant 1

HCID 86690096HCID 86690096, compound

Product 1

HCID 534038373,3-Difluorocyclopentane-1-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (S)-1-phenylethyl 3,3-difluorocyclopentanecarboxylate (diastereomer-1 or diastereomer-2, 0.15 g) in ethanol (5 mL) was added 10% Pd—C. The reaction mixture was stirred at rt under H2 for 16 h. The reaction mixture was filtered and the filtrate was concentrated to afford corresponding enantiomers of 3,3-difluorocyclopentanecarboxylic acid. 1H NMR (400 MHz, METHANOL-d4) ppm 2.97-3.08 (1H, m), 2.28-2.41 (2H, m), 1.93-2.23 (4H, m).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d590978582dc4a63b850f86b8168f309
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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