Hexane → HCID 68580593, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 9-bromo-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (200 mg, 0.605 mmol) in tetrahydrofuran (4 ml) was added dropwise 1.6 M solution of n-butyllithium in hexane (0.396 ml, 0.634 mmol) at −78° C., and the mixture was stirred at −78° C. for 10 min. A solution of cyclopentanone (0.0696 ml, 0.787 mmol) in tetrahydrofuran (2 ml) was added dropwise, and the mixture was stirred at 78° C. for 2 hr. The reaction mixture was poured into saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and 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 (30.0 mg, 14.9%) as an oil.

Provenance & Evidence