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

Participants

Reaction Steps

To a solution of 1-diphenylmethylazetidin-3-ol (see Preparation 3(a)) (65.9 g, 275.7 mmol) in dry dichloromethane (700 ml) at 0° C. under nitrogen was added triethylamine (57 ml, 1.5 mol. equiv.). After five minutes, methanesulphonyl chloride (25.6 ml, 1.2 mol. equiv.) was added and the mixture stirred for one hour. Water (300 ml) was then added and the mixture extracted with dichloromethane (3×300 ml). The combined organic layers were dried over magnesium sulphate. The solution was then filtered and the solvent removed from the filtrate by evaporation under reduced pressure. The residue was chromatographed using silica gel eluting with methanol:dichloromethane (1:49, by volume) to give the title compound (73.4 g) as a solid.

Provenance & Evidence