Ammonium Chloride → Benzyl 4-(2-hydroxyethoxy)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of sodium borohydride (10.1 g), calcium chloride (13.3 g), ethanol (100 mL) and THF (50 mL) was stirred at 0° C. for 30 min. After stirring, a mixture of benzyl 4-(2-ethoxy-2-oxoethoxy)piperidine-1-carboxylate (9.68 g) and THF (50 mL) was added dropwise at 0° C., and the obtained mixture was stirred at room temperature for 2 days. Saturated aqueous ammonium chloride solution was added thereto, and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure. The residue was extracted with ethyl acetate, and the extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (6.33 g).

Provenance & Evidence