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

Participants

Reaction Conditions

Reaction Steps

Triethylamine (24.7 mL) was added to a solution of 1-benzhydrylazetidin-3-ol (5 g) in DMSO (25 mL). A solution of pyridine sulphur trioxide (18 g) in DMSO (65 mL) was added dropwise and the mixture stirred at 20° C. for 90 minutes. The mixture was poured onto ice/water and extracted twice with ethyl acetate, the combined organics were washed three times with brine before being dried over sodium sulphate, filtered and the solvent removed under reduced pressure. The crude product was purified by flash silica chromatography using 2% triethylamine in isohexane as solvent. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 2.9 g.

Provenance & Evidence