Disodium 2,3-dihydroxybutanedioate → Benzyl 4-formylpiperidine-1-carboxylate

Participants

Reaction Steps

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.

Provenance & Evidence