Ammonia → HCID 18378679, compound

Participants

Reaction Steps

To an ice-bath-cooled solution of methyl 2-methoxy-4-(2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)carbonylbenzoate (350 mg) in tetrahydrofuran (15 ml) was added dropwise a 1M solution of borane-tetrahydrofuran complex (3.1 ml), and the mixture was stirred at room temperature for 6 hours. After quenching the reaction with 1N hydrochloric acid (10 ml), the mixture was adjusted to pH 8-9 with concentrated ammonia solution and extracted with chloroform. The solution was washed with brine. The organic layer was dried over magnesium sulfate and the solvent was evaporated in vacuo. The crude product was purified by silica gel column chromatography (10% ethyl acetate in hexane) to give methyl 2-methoxy-4-(2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)methylbenzoate (255 mg).

Provenance & Evidence