5-[(1S,6S)-4,4-Difluoro-7-oxabicyclo[4.1.0]hept-1-yl]-1-methyl-1H-pyrazole → (1S,2R)-5,5-Difluoro-2-(1-methyl-1H-pyrazol-5-yl)cyclohexanol

HRID 337886Notes

Reaction equation

HRID 337886 reaction equation
[F:1][C:2]1([F:15])[CH2:8][C@H:7]2[C@:5]([C:9]3[N:13]([CH3:14])[N:12]=[CH:11][CH:10]=3)([O:6]2)[CH2:4][CH2:3]1>[Ni].C(O)(C)C>[F:15][C:2]1([F:1])[CH2:8][C@H:7]([OH:6])[C@@H:5]([C:9]2[N:13]([CH3:14])[N:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 899627535-[(1S,6S)-4,4-Difluoro-7-oxabicyclo[4.1.0]hept-1-yl]-1-methyl-1H-pyrazole

Product 1

HCID 89962726(1S,2R)-5,5-Difluoro-2-(1-methyl-1H-pyrazol-5-yl)cyclohexanolYield 42.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 3776IsopropanolSolvent

Procedure

A solution of the 5-[(1S,6S)-4,4-difluoro-7-oxabicyclo[4.1.0]hept-1-yl]-1-methyl-1H-pyrazole (50 mg, 0.233 mmol) prepared in Example 102b and Raney nickel (500 mg) in isopropanol (20 mL) was stirred for 3 hours under a hydrogen atmosphere. The reaction solution was filtered, the filtrate was concentrated, and the residue was then purified with silica gel chromatography to yield the title compound (21.2 mg, 42%) as a colorless oil.

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationthe filtrate was concentrated
  3. customthe residue was then purified with silica gel chromatography

Sources & evidence

ORD record
ord-4c77ba7863684cff97aa0a6ffbf01c77
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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