N-bromobutanimide → HCID 9934776, compound

Participants

Reaction Steps

A suspension of 3-tert-butoxycarbonyl-1-(3-fluorobenzyl)-8-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepine-2-one (1.00 g, 2.503 mmol) and NBS (0.49 g, 2.754 mmol) in acetic acid (0.8 mL) and chloroform (8 mL) was heated at reflux for 4 hrs. The reaction mixture was allowed to cool to room temperature, diluted with DCM (30 mL), washed with saturated aqueous sodium bicarbonate solution, dried over Na2SO4. Filtration and evaporation of the organic layer gave a solid residue, which was purified by flash chromatography on silica column eluted with ethyl acetate/n-hexane (25% of ethyl acetate in n-hexane). The title compound was obtained as a white powder (0.400 g, 33%).

Provenance & Evidence