Methanesulfonyl chloride → 1-Benzhydryl-3-methylazetidin-3-yl methanesulfonate

Participants

Reaction Conditions

Reaction Steps

10 g (0.0394 mol) of 1-benzhydryl-3-methylazetidin-3-ol (S. S. Chattergee and A. Shoeb, Synthesis 1973, p. 153-154) are dissolved in 100 ml of anhydrous pyridine, the mixture is cooled to -20° C. and 7.3 g (0.063 mol) of methanesulphonyl chloride are added dropwise. The temperature is kept below -10° C., stirring is carried out at this temperature for 1 hour and the reaction mixture is left between 0° C. and 3° C. for two days. It is poured into 600 ml of water/ice, the precipitate is recovered by filtration and is washed with water. After drying in the oven at 50° C. for 2 hours the product is taken up in isopropyl ether (100 ml), is filtered and is dried in the oven at 50° C. overnight to obtain approximately 10 g of 1-benzhydryl-3-methanesulphonyloxy-3-methylazetidine.

Provenance & Evidence