Tetrahydrofuran → Pyrido-[3,4-f][1,4]-diazepin-3-yl cyclopropyl carbinol

Participants

Reaction Steps

To a solution of cyclopropyl magnesium bromide in dry tetrahydrofuran (prepared from 72 mg (3 mmole)) of magnesium and 362 mg (3 mmole) of cyclopropyl bromide in 4 ml of tetrahydrofuran was added at room temperature in one portion a suspension of 240 mg (1 mmole)of 5,6-dihydro-5-methyl-6-oxo-4H-imidazo [1,5-a]-pyrido [3,4-f][1,4]-diazepine-3-carboxaldehyde suspended in a mixture of 1 ml of tetrahydrofuran and 1 ml of hexamethyl-phosphoramide. After 1 hour, the reaction was quenched with aqueous ammonium chloride and extracted with dichloromethane. Column chromatography (SiO2 -5% methanol in dichloromethane) yielded 120 mg of 5,6-dihydro-5-methyl-6-oxo-4H-imidazo-1,5-a]-pyrido-[3,4-f][1,4]-diazepin-3-yl cyclopropyl carbinol as an oil, (43%).

Provenance & Evidence