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

HRID 432283Notes

Reaction equation

HRID 432283 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-d) 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-7b1f14bb50434a5aa3b266c191fb08f0
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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