Water → 1-Benzhydryl-3-(methylsulfonyl)azetidine

Participants

Reaction Steps

To a cold solution of 34 g (0.142 mol) of 1-(diphenylmethyl)-3-hydroxyazetidine in 200 mL of CH2Cl2 was added 30 mL (212 mol) of triethylamine. To the cold mixture a solution of 19.5 g (0.171 mol) of methanesulfonyl chloride in 50 mL of CH2Cl2 was added dropwise. The reaction was stirred at room temperature for 2 h. Water was added and the methylene chloride was removed under vacuo. The product was extracted with ether, the combined extracts were dried over anhydrous sodium sulfate, and filtered to yield 36 g of product. 1H NMR (300 MHz, CDCl3) δ 2.98 (s, 3H), 3.21 (m, 2H), 3.66 (m, 2H), 4.39 (s, 3H), 5.10 (m, 1H), 7.22 (m, 2H), 7.27 (m, 4H), 7.38 (m, 4H).

Provenance & Evidence