Dimethyl Sulfoxide → 1-(Diphenylmethyl)azetidin-3-one

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of DMSO (12.45 ml, 176 mmol) in DCM (150 mL) at −78° C. under an argon atmosphere was added dropwise oxalyl chloride (8.61 mL, 100 mmol). After stirring for 30 minutes at −78° C., a solution of 1-benzhydrylazetidin-3-ol (20 g, 84 mmol) in DCM (75 mL) was added dropwise. The reaction mixture was stirred for 1 h at −78° C. before triethylamine (58.2 ml, 418 mmol) was added. The reaction mixture was allowed to reach 0° C. and was quenched with saturated NH4Cl (150 mL), and then extracted with DCM (3×). The combined organic layers were washed with water, brine, dried on Na2SO4 and concentrated to give crude 1-benzhydrylazetidin-3-one (20.8 g, 105%) as a yellow solid.

Provenance & Evidence