Methanol → (1S*,2R*)-4,4-Difluoro-2-(1-methyl-1H-pyrazol-5-yl)cyclohexanol

HRID 337859Notes

Reaction equation

HRID 337859 reaction equation
[F:1][C:2]1([F:15])[CH2:7][CH2:6][C:5](=[O:8])[C:4]([C:9]2[N:13]([CH3:14])[N:12]=[CH:11][CH:10]=2)=[CH:3]1.[BH4-].[Na+].CO>[C+4].[OH-].[Pd+2].[OH-].[OH-].[OH-].[OH-].[OH-].C(O)C>[F:15][C:2]1([F:1])[CH2:7][CH2:6][C@H:5]([OH:8])[C@@H:4]([C:9]2[N:13]([CH3:14])[N:12]=[CH:11][CH:10]=2)[CH2:3]1

Participants

6

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 899629404,4-Difluoro-2-(1-methyl-1H-pyrazol-5-yl)cyclohex-2-en-1-one

Product 1

HCID 89963011(1S*,2R*)-4,4-Difluoro-2-(1-methyl-1H-pyrazol-5-yl)cyclohexanolYield 29%

Reagents, catalysts & solvents 2

HCID 178420936HCID 178420936, compoundCatalystHCID 702EthanolSolvent

Procedure

The reaction and aftertreatment were conducted in the same manner as in Example 67d by using the 4,4-difluoro-2-(1-methyl-1H-pyrazol-5-yl)cyclohex-2-en-1-one (170 mg, 0.80 mmol) prepared in Example 88f, sodium borohydride (60 mg, 1.59 mmol), methanol (3.0 mL), palladium hydroxide carbon (10%; 150 mg) and ethanol (4.0 mL), to yield the title compound (50 mg, 29%) as a colorless solid.

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-add4bf05207c4c8aa4d5e5316f6d7287
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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