Methyl iodide → tert-Butyl 3-methoxyazetidine-1-carboxylate

Participants

Reaction Steps

To a solution of tert-butyl 3-hydroxyazetidine-1-carboxylate (J. Med. Chem. 2001, 44, 94., 130 mg, 0.75 mmol) in tetrahydrofuran (1.5 mL) was added sodium hydride (60% in mineral oil dispersion, 36 mg, 0.90 mmol) slowly at 0° C. After 30 min., iodomethane (130 mg, 0.90 mmol) was added to the mixture at 0° C. The mixture was gradually warmed to room temperature and stirred overnight. The mixture was concentrated and purified by column chromatography on silica gel eluting with hexane/ethyl acetate (6/1) to afford 110 mg (76%) of the title compound as a colorless oil:

Provenance & Evidence