tert-Butyl 4-formylpiperidine-1-carboxylate → Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate
Reaction equation
[CH:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)=[O:2].[BH4-].[Na+]>C1COCC1>[OH:2][CH2:1][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 0.434 g of 4-formyl-piperidine-1-carboxylic acid, tert-butyl ester (from Step A) in 15 ml THF was added sodium borohydrid at 0° C. and stirred at 0° C. for 20 mn. The reaction was warmed to rt and stirred at rt for 14 hours. After quenching with CH3OH, the reaction mixture was concentrated, then partitioned between EtOAc and H2O. The aqueous layer was extracted with 2×20 mL of EtOAc. The combined organic phases were washed with brine, dried over MgSO4 and concentrated. The residue was purified by flash chromatography eluting with 50% EtOAc in hexane, then 100% EtOA to give 390 mg of the title compound as an oil.
Workup
- temperatureThe reaction was warmed to rt
- stirringstirred at rt for 14 hours
- customAfter quenching with CH3OH
- concentrationthe reaction mixture was concentrated
- custompartitioned between EtOAc and H2O
- extractionThe aqueous layer was extracted with 2×20 mL of EtOAc
- washThe combined organic phases were washed with brine
- dry with materialdried over MgSO4
- concentrationconcentrated
- customThe residue was purified by flash chromatography
- washeluting with 50% EtOAc in hexane
Sources & evidence
- ORD record
- ord-9efc596fe4114e43b9f6c3b8657e0635
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06265434B1
Reaction notes
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