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

HRID 897703Notes

Reaction equation

HRID 897703 reaction equation
[BH4-].[Na+].[O:3]=[C:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1>CO>[OH:3][CH:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH2:9]1

Participants

4

Reactant 2

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

Product 1

HCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateYield 101.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (3.8 g, 100.4 mmol) was added in portions to a solution of tert-butyl 4-oxo-1-piperidinecarboxylate (20 g, 100.4 mmol) in methanol (600 mL) at 0° C. After 15 minutes, the ice-water bath was removed and the reaction mixture was stirred at room temperature for 3 hours. Sodium hydroxide (1.0 N, 100 mL) was added and the organic solvent was evaporated. The aqueous was extracted with ether four times. The combined organic layer was washed with water then brine, dried over MgSO4, filtered and evaporated to give tert-butyl 4-hydroxy-1-piperidinecarboxylate (20.48 g, 100%). 1H NMR (CDCl3) δ 1.48 (s, 9H), 1.63 (m, 2H), 1.87 (m, 2H), 3.03 (m, 2H), 3.83 (m, 3H).

Workup

  1. customthe ice-water bath was removed
  2. additionSodium hydroxide (1.0 N, 100 mL) was added
  3. customthe organic solvent was evaporated
  4. extractionThe aqueous was extracted with ether four times
  5. washThe combined organic layer was washed with water
  6. dry with materialbrine, dried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-89082217ca174999a3d19709d5e29382
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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