Methanesulfonyl chloride → HCID 86727621, compound

Participants

Reaction Steps

To a mixture of TEA (30 g, 296 mmol) and 1-benzhydryl-3-methyl-azetidin-3-ol (30 g, 118 mmol) in DCM (300 mL) at 0° C. was added a solution of methanesulfonyl chloride (20.49 g, 179 mmol) in DCM (15 mL) keeping the internal temperature below 5° C. The mixture was stirred at ambient temperature for 20 h and quenched by addition of water (50 mL). The organic phase was separated, dried over anhydrous Na2SO4 and evaporated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 0% EtOAc to 50% EtOAc in petroleum ether) to give 1-benzhydryl-3-chloro-3-methyl-azetidine (7 g, 22%): 1H NMR (CDCl3, 400 MHz): δ7.42-7.45 (m, 4H), 7.27-7.31 (m, 4H), 7.18-7.23 (m, 2H), 4.48 (s, 1H), 3.38-3.44 (m, 4H), 1.87 (s, 3H) and methanesulfonic acid 1-benzhydryl-3-methyl-azetidin-3-yl ester (16 g, 41%). 1H NMR (CDCl3, 400 MHz): δ7.40-7.37 (m, 4H), 7.20-7.28 (m, 4H), 7.16-7.20 (m, 2H), 4.42 (s, 1H), 3.33 (s, 4H), 3.02 (s, 3H), 1.90 (s, 3H).

Provenance & Evidence