Triethylamine → 1-(Diphenylmethyl)azetidin-3-one

Participants

Reaction Conditions

Reaction Steps

1-(Diphenylmethyl)azetidin-3-ol (2.0 g) was dissolved in N,N-dimethyl sulfoxide (60 mL), and triethylamine (11.7 mL) was added. The reaction solution was cooled to 10° C., a solution of pyridine sulfur trioxide complex (10.6 g) in N,N-dimethyl sulfoxide (20 mL) was added, and the mixture was stirred for 1 hr. The mixture was warmed to room temperature and further stirred for 3 hr. The reaction solution was poured into cold water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over sodium sulfate. The desiccant was filtered off, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (30% to 50% ethyl acetate/hexane) to give the object product as a white solid (1.83 g, 92.4%).

Provenance & Evidence