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

HRID 919210Notes

Reaction equation

HRID 919210 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[BH4-].[Na+]>CO>[OH:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1

Participants

4

Reactant 2

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

Product 1

HCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateYield 97.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 4-oxopiperidine-1-carboxylate (10 g, 50 mmol) in CH3OH (100 mL) was added NaBH4 (5.7 g, 150 mmol) portionwise carefully and the mixture was stirred at rt for 3 h. The reaction was quenched by carefully pouring into ice-water (100 mL) and organic solvent was removed under reduced pressure. The aqueous phase was neutralized to pH=7 with 1N HCl and extracted with DCM/MeOH (5×60 mL, v/v=10/1). The combined organic layers were washed with brine (30 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford the crude product (9.8 g, 97%) as a white solid. [LCMS: Rt=1.36 min, m/z 146.1 (M−Bu+H)+].

Workup

  1. customThe reaction was quenched
  2. additionby carefully pouring into ice-water (100 mL) and organic solvent
  3. customwas removed under reduced pressure
  4. extractionextracted with DCM/MeOH (5×60 mL, v/v=10/1)
  5. washThe combined organic layers were washed with brine (30 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-451fc4374086424eb841cd0458b7e330
Source dataset
uspto-grants-2016_03
Patent number
US09273026B2

Reaction notes

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