(+)-Benzyl 3,3-difluoro-1-hydroxycyclopentanecarboxylate → (+)-3,3-Difluoro-1-hydroxycyclopentanecarboxylic acid

HRID 1160608Notes

Reaction equation

HRID 1160608 reaction equation
[F:1][C:2]1([F:18])[CH2:6][CH2:5][C:4]([OH:17])([C:7]([O:9]CC2C=CC=CC=2)=[O:8])[CH2:3]1>CCOC(C)=O.[Pd]>[F:1][C:2]1([F:18])[CH2:6][CH2:5][C:4]([OH:17])([C:7]([OH:9])=[O:8])[CH2:3]1

Participants

4

Reactant 1

HCID 68718275(+)-Benzyl 3,3-difluoro-1-hydroxycyclopentanecarboxylate

Product 1

HCID 68715806(+)-3,3-Difluoro-1-hydroxycyclopentanecarboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of (+)-benzyl 3,3-difluoro-1-hydroxycyclopentanecarboxylate (1.8 g, 7.0 mmol) in 45 ml of EtOAc was added a suspension of 10% Palladium on Carbon (720 mg) in 5 ml of EtOAc. The mixture was stirred at room temperature under hydrogen atmosphere for 1 hour (balloon). The reaction mixture was filtered through a glass micropore filter to remove the catalyst and the filtrate was concentrated under vacuum to give (+)-3,3-difluoro-1-hydroxycyclopentanecarboxylic acid.

Workup

  1. filtrationThe reaction mixture was filtered through a glass micropore
  2. filtrationfilter
  3. customto remove the catalyst
  4. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-dff7e9ce51a14210ac47df6311e62170
Source dataset
uspto-grants-2010_10
Patent number
US07816380B2

Reaction notes

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