反应详情

Add diisobutyl aluminum hydride (1 M in toluene, 30 mL, 30 mmol) over 5 minutes to a solution of 1-(benzyloxycarbonyl)-4-(ethoxycarbonyl)piperidine (7 g, 24 mmol) in anhydrous dichloromethane (150 mL) at −78° C. under a nitrogen atmosphere. Stir the reaction mixture at this temperature for 30 minutes and then add 10% aqueous sodium tartarate (100 mL) followed by dichloromethane. Stir the reaction mixture at room temperature overnight. Separate the phases and extract the aqueous phase with dichloromethane. Wash the combined organic phases sequentially with 10% aqueous sodium tartarate, water, and saturated aqueous sodium chloride. Dry over sodium sulfate and concentrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with 3:1 hexanes:ethyl acetate to provide 3.15 g (53%) of the title compound.

1. stirringStir the reaction mixture at room temperature overnight
2. customSeparate the phases
3. extractionextract the aqueous phase with dichloromethane
4. washWash the combined organic phases sequentially with 10% aqueous sodium tartarate, water, and saturated aqueous sodium chloride
5. dry with materialDry over sodium sulfate
6. concentrationconcentrate under reduced pressure
7. washeluting with 3:1 hexanes