1-(Diphenylmethyl)azetidin-3-yl methanesulfonate → 1-(Diphenylmethyl)-3-phenylazetidine

Participants

Reaction Steps

Under nitrogen mix copper (I) bromide (1.1 g, 7.6 mmol) and anhydrous THF (20 mL). Add a 3.0 M solution of phenylmagnesium bromide in ether slowly (2.5 mL, 7.6 mmol). Stir at RT for 90 min. Dissolve 1-(diphenylmethyl)-3-(methanesulphonyloxy)azetidine (2.0 g, 6.3 mmol) in anhydrous THF (10 mL) and transfer to the reaction mixture. Heat at 50° C. then stir at RT for 16 h. Dilute with EtOAc and wash with saturated aqueous sodium bicarbonate solution. Separate organic layer, dry (sodium sulfate), concentrate and purify (silica gel chromatography, eluting 10:90 EtOAc:hexanes) to give the title compound (515 mg, 27%).

Provenance & Evidence