Methanesulfonyl chloride → Tert-butyl 3-(methanesulfonyloxy)azetidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of tert-butyl 3-hydroxyazetidine-1-carboxylate A1a (2 g, 11.5 mmol) in dichloromethane (0.5M, 23 mL) is treated with ethyldiisopropylamine (3 mL, 17.5 mmol) and the mixture is cooled to 0° C. Methanesulfonyl chloride (0.99 mL, 12.7 mmol) is then added dropwise and the mixture is allowed to stir at room temperature for 6 hours. The mixture is diluted with dichloromethane, washed with 1M HCl, brine, dried over sodium sulfate and concentrated in vacuo to afford tert-butyl 3-(methylsulfonyloxy)azetidine-1-carboxylate A1b as oil that solidifies upon standing: 1H-NMR (400 MHz, CDCl3) δ=5.25-5.19 (m, 1H), 4.30 (ddd, J=10.4, 6.4, 1.2 Hz, 2H), 4.12 (ddd, J=10.4, 4.0, 1.2 Hz, 2H), 3.09 (s, 3H), 1.46 (s, 9H); MS calcd. for C9H18NO5S ([M+H]+): 252.1, found: 252.2. The product is used without purification.

Provenance & Evidence