Ethyl Acetate → 3-Ethyl-2,3,9,10,11,12-hexahydro-1H-quino[4,3,2-ef][1,4]benzoxazepine fumarate

Participants

Reaction Steps

To a solution of lithium aluminum hydride in tetrahydrofuran (1M, 14.8 ml) and dry tetrahydrofuran (30 ml) was added aluminum chloride (1.89 g) in portions, with stirring. After 5 mins, 3-ethyl-1,3,9,10,11,12-hexahydro-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one (4.0 g) was added, and the reaction mixture was stirred at room temperature overnight. Ethyl acetate (200 ml) and 10% sodium hydroxide solution (200 ml) were added. The organic phase was separated, dried over magnesium sulfate, filtered, and the filtrate was concentrated. The residue was flash chromatographed (5% triethylamine/toluene). The appropriate fractions were concentrated and treated with fumaric acid to give 4.05 g (74%) of product, mp 210° C.

Provenance & Evidence