Ammonium Chloride → 4-(Benzyloxy)-2-fluorocyclohexanol

HRID 1970984Notes

Reaction equation

HRID 1970984 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][C:12](=[O:15])[CH:11]([F:16])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].[Cl-].[NH4+]>CO.[Cl-].[Na+].O>[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([OH:15])[CH:11]([F:16])[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 59543141(2RS,4SR)-4-(Benzyloxy)-2-fluoro-cyclohexan-1-one

Product 1

HCID 595431264-(Benzyloxy)-2-fluorocyclohexanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred solution of 4-(benzyloxy)-2-fluorocyclohexanone (3.8 g, 17.1 mmol) in methanol (60 mL) was added sodium borohydride (1.29 g, 34.2 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature, and left to stir for 45 min. The reaction mixture was treated with ammonium chloride solution and brine, and extracted with EtOAc. The combined organics were dried (magnesium sulfate), and concentrated to afford the title compound.

Workup

  1. waitleft
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organics were dried (magnesium sulfate)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a8140fedebcb464498345906b84fc9d9
Source dataset
uspto-grants-2013_04
Patent number
US08431569B2

Reaction notes

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