tert-Butyl 4-oxopiperidine-1-carboxylate → Tert-butyl 4-hydroxypiperidine-1-carboxylate
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 1-t-butoxycarbonyl-4-piperidone (3.00 g) in ethanol was added sodium borohydride (854 mg) under ice-water cooling and the mixture was stirred at 0° C. for 2 hours. After evaporation of solvent, ethyl acetate and water were added. The organic layer was separated, washed with dilute hydrochloric acid, water, saturated sodium bicarbonate solution and brine, dried over magnesium sulfate, and evaporated in vacuo to give 1-t-butoxycarbonyl-4-hydroxypiperidine as colorless oil (3.15 g).
Workup
- customAfter evaporation of solvent, ethyl acetate and water
- additionwere added
- customThe organic layer was separated
- washwashed with dilute hydrochloric acid, water, saturated sodium bicarbonate solution and brine
- dry with materialdried over magnesium sulfate
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-f2b7eb713c3e4d17bec865756f848a6f
- Source dataset
- uspto-grants-2005_11
- Patent number
- US06967197B2
Reaction notes
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