N-Acetyl-4-piperidone → 1-(4-Hydroxypiperidin-1-yl)ethan-1-one

HRID 1590201Notes

Reaction equation

HRID 1590201 reaction equation
[BH4-].[Na+].[C:3]([N:6]1[CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH2:7]1)(=[O:5])[CH3:4]>C(O)(C)C>[C:3]([N:6]1[CH2:11][CH2:10][CH:9]([OH:12])[CH2:8][CH2:7]1)(=[O:5])[CH3:4]

Participants

4

Reactant 2

HCID 122563N-Acetyl-4-piperidoneHCID 4311764Sodium borohydride

Product 1

HCID 107492911-(4-Hydroxypiperidin-1-yl)ethan-1-oneYield 100%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a cooled (0° C.) mixture of NaBH4 (2.15 g, 0.057 mol) and isopropanol (70 mL) was added N-acetyl-4-piperidone (8.00 g, 0.057 mol). The mixture was allowed to warm to room temperature and stirred for 16 hours. CO2 was bubbled into the reaction mixture, EtOAc (120 mL) was added, and the precipitate was removed by filtration. The filtrate was concentrated to give 8.0 g (100%) of N-acetyl-4-hydroxypiperidine as a colorless oil.

Workup

  1. temperatureTo a cooled
  2. customCO2 was bubbled into the reaction mixture, EtOAc (120 mL)
  3. additionwas added
  4. customthe precipitate was removed by filtration
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-36270597bfd44a20aadce73d58d0792b
Source dataset
uspto-grants-1993_04
Patent number
US05202346

Reaction notes

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