1-Benzyl-3,3-difluoropiperidin-4-ol → 3,3-Difluoropiperidin-4-OL

HRID 2280372Notes

Reaction equation

HRID 2280372 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[C:10]([F:16])([F:15])[CH2:9]1)C1C=CC=CC=1>CCO.[OH-].[OH-].[Pd+2]>[F:15][C:10]1([F:16])[CH:11]([OH:14])[CH2:12][CH2:13][NH:8][CH2:9]1

Participants

4

Reactant 1

HCID 594427361-Benzyl-3,3-difluoropiperidin-4-ol

Product 1

HCID 552996013,3-Difluoropiperidin-4-OL

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar, a suspension of 1-benzyl-3,3-difluoropiperidin-4-ol (1.73 g, 7.62 mmol) and Pd(OH)2 (20% Pd, 107 mg) in dry EtOH (50 mL) was stirred at rt under a H2 atmospheric pressure until completion of the reaction. The mixture was then filtered, washed with EA/EtOH, and the filtrate concentrated under reduced pressure to give the title compound as a beige solid. LC-MS-conditions 08: tR=0.15 min; [M+H]+=138.27.

Workup

  1. customIn a flame dried round-bottomed flask equipped with a magnetic stir bar
  2. customuntil completion of the reaction
  3. filtrationThe mixture was then filtered
  4. washwashed with EA/EtOH
  5. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-4ccd7589e0714213be0d5f8b5abb7c68
Source dataset
uspto-grants-2015_09
Patent number
US09139524B2

Reaction notes

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