tert-Butyl 4-oxopiperidine-1-carboxylate → Tert-butyl 4-hydroxypiperidine-1-carboxylate

HRID 2403381Notes

Reaction equation

HRID 2403381 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[BH4-].[Na+]>C(O)C>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:2])([CH3:7])([CH3:5])[CH3:6]

Participants

4

Reactant 2

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateYield 91.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To 1-Boc-4-piperidone (10 g) in ethanol stirring at 0° C. was added sodium borohydride (9.45 g) portionwise. The reaction mixture was stirred at 0° C. for 1 hour. The reaction mixture was then quenched with water and extracted with chloroform. The combined organic were washed with brine and dried (MgSO4). The solvent was removed in vacuo to yield 9.2 g of 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. customThe reaction mixture was then quenched with water
  2. extractionextracted with chloroform
  3. washThe combined organic were washed with brine
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-42a8eb31bb2647d4b856b491670eacdf
Source dataset
uspto-grants-2014_08
Patent number
US08802670B2

Reaction notes

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