Benzhydrylamine → 1-Benzhydryl-3-methylazetidin-3-ol

Participants

Reaction Steps

Diphenylmethanamine (68.8 mL, 375 mmol) was added dropwise into a solution of 2-(chloromethyl)-2-methyloxirane (40 g, 375 mmol) in methanol (160 mL) and the reaction was stirred at rt for 72 h and then at reflux for 20 h. The reaction was cooled to ambient temperature, evaporated in vacuo and suspended in acetone (200 mL). The solid was collected by filtration to give 1-benzhydryl-3-methyl-azetidin-3-ol (60 g, 63%) as a white solid. 1H NMR (DMSO-d6, 400 MHz): δ7.61 (m, 4H), 7.31 (m, 6H), 6.43 (m, 1H), 6.00 (m, 1H), 3.80-4.00 (m, 4H), 1.45 (m, 3H).

Provenance & Evidence