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

Participants

Reaction Steps

Slowly add 1.0 mole of methanesulfonyl chloride to an agitating solution of 1.0 mole 1-benzhydryl-3-hydroxyazetidine and triethylamine in benzene or toluene maintained at 10° to 15° C. Agitate the reaction mixture at 15° to 18° C. for half an hour, then at 20°-23° C. for another half hour. Add diethyl ether and agitate for 10 minutes longer. Remove the triethylamine hydrochloride precipitate by filtration and add the filtrate to a solution of 1.0 mole maleic acid in diethyl ether and stir for about one hour. Isolate the product 1-benzhydryl-3-methanesulfonyloxyazetidine as the hemimaleate salt (1:1) by filtration.

Provenance & Evidence