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

Participants

Reaction Steps

Triethylamine (1.80 ml) was added to a solution of tert-butyl 3-(hydroxymethyl)azetidine-1-carboxylate (806 mg) in tetrahydrofuran (25 ml). This was cooled on ice under a nitrogen atmosphere, and methanesulfonyl chloride (0.499 ml) was added dropwise, followed by stirring at the same temperature for 30 minutes. The reaction mixture was partitioned after the addition of ethyl acetate (100 ml) and water (70 ml). The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (eluent; ethyl acetate). The fractions containing the target compound were concentrated to give the title compound (1.05 g, 92.0%) as a colorless oil.

Provenance & Evidence