Hexane → HCID 68579723, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 9-bromo-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (328 mg, 1.00 mmol) in tetrahydrofuran (3 ml) was added 1.6N solution of n-butyllithium in hexane (0.829 ml, 1.33 mmol) at −78° C., and the mixture was stirred at −78° C. for 15 min. At −78° C., a solution of cyclobutanone (0.0747 ml, 1.00 mmol) in tetrahydrofuran (1 ml) was added, and the mixture was stirred at −78° C. for 30 min. Saturated aqueous ammonium chloride solution (3 ml) was added, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give the desired product (108 mg, 33.8%) as an oil.

Provenance & Evidence