Triethylamine → Tert-butyl 3-(methanesulfonyloxy)azetidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 3-hydroxyazetidine-1-carboxylate (6.0 g, 34.68 mmol) in DCM was added by Et3N. The mixture was cooled to 0° C. and methanesulfonyl chloride was slowly added. After addition was complete, the reaction mixture was warmed to RT and stirred until starting material was completely consumed as indicated by TLC (40% EtOAc/hexanes). The reaction mixture was filtered and CH2Cl2 was added to the filtrate (100 mL). The organics were washed with water (2×30 mL), brine solution (30 mL), dried (Na2SO4), filtered, and concentrated to obtain crude product, which was purified by silica gel chromatography (5% EtOAc/hexanes, then 15% EtOAc/hexanes). 1-(tert-Butoxycarbonyl)azetidin-3-yl methanesulfonate was isolated as an off-white solid (2.2 g, 36% yield); ES-MS: 252.08 (M+H).

Provenance & Evidence