Ethanol → Tert-butyl 3-fluoro-4-hydroxypiperidine-1-carboxylate

HRID 2193114Notes

Reaction equation

HRID 2193114 reaction equation
C(O)C.[F:4][CH:5]1[C:10](=[O:11])[CH2:9][CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6]1.[BH4-].[Na+].O>C(OCC)(=O)C>[F:4][CH:5]1[CH:10]([OH:11])[CH2:9][CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6]1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 10560711TERT-BUTYL 3-FLUORO-4-OXOPIPERIDINE-1-CARBOXYLATE

Product 1

HCID 42609254Tert-butyl 3-fluoro-4-hydroxypiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 6.5 mL of an ethanol solution containing 0.49 g of tert-butyl 3-fluoro-4-oxopiperidine-1-carboxylate, 94 mg of sodium borohydride was added under cooling with ice, and the mixture was stirred for 1 hour. The reaction mixture was added with water and ethyl acetate. The organic layer was separated, washed with an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 0.42 g of a colorless oily substance, tert-butyl 3-fluoro-4-hydroxypiperidine-1-carboxylate.

Workup

  1. additionwas added
  2. temperatureunder cooling with ice
  3. customThe organic layer was separated
  4. washwashed with an aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-157798d13cf64890b88009849d1d9dda
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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