Triethylamine → 1-Benzhydryl-3-methylazetidin-3-yl methanesulfonate

Participants

Reaction Conditions

Reaction Steps

To a slurry of 1-benzhydryl-3-methylazetidin-3-ol hydrochloride (10.00 g, 34.54 mmol) in dichloromethane (80 ml) was added triethylamine (8.00 g, 79.20 mmol) and the mixture cooled to 0° C. Methanesulfonyl chloride (5.20 g, 45.41 mmol) was added dropwise and the reaction mixture was then allowed to warm to room temperature and stirred for 4 hrs. The reaction was diluted with water and dichloromethane and the organic layer was washed further with water, brine then dried (MgSO4) and concentrated to give a pale pink solid. The solid was purified on silica gel eluting with 20% ethyl acetate/petrol to provide the title compound as a white solid (1.69 g, 64%). 1H NMR (CDCl3) 1.92 (3H, s), 3.05 (3H, s), 3.33 (4H, s), 4.42 (1H, s), 7.18-7.20 (2H, m), 7.23-7.30 (4H, m), 7.39-7.52 (4H, m).

Provenance & Evidence