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

Participants

Reaction Steps

Triethylamine (57 ml, 1.5 mol equivalent) was added to a solution of 1-diphenylmethylazetidin-3-ol (65.9 g, 275.7 mmol) in dry dichloromethane (700 ml) at 0° C. under nitrogen. After five minutes, methanesulphonyl chloride (25.6 ml, 1.2 mol equivalent) was added and the mixture stirred for one hour. Water (300 ml) was added and the mixture extracted with dichloromethane (3×300 ml). The combined organic layers were dried over magnesium sulphate and the solvent removed under reduced pressure. The residue was chromatographed on silica gel eluting with methanol:dichloromethane (1.49, by volume) to give the title product (73.4 g) as a solid. 1H-NMR (CDCl3): δ=2.95(s,3H), 3.15-3.25(m,2H), 3.6-3.65(m,2H), 4.4(s,1H), 5.05-5.15(m,1H), 7.15-7.4(m,10H)ppm.

Provenance & Evidence