Potassium Carbonate → (S)-8-chloro-11,12,13,13a-tetrahydro-1-(5-oxazolyl)-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one

Participants

Reaction Steps

A mixture of 1.51 g (5 mmol) of (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxaldehyde, 1.07 g (5.5 mmol) of toluene-4-sulphonylmethyl isocyanide, 1 g of powdered potassium carbonate and 20 ml of methanol is heated to boiling under reflux for 2 hours. The mixture is then evaporated to a volume of 5 ml and the material obtained is chromatographed on silica gel while eluting with ethyl acetate/methanol (9:1). After recrystallization from ethyl acetate there is obtained (S)-8-chloro-11,12,13,13a-tetrahydro-1-(5-oxazolyl)-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one of melting point 201°-202°.

Provenance & Evidence