Cyclohexanol → HCID 54468936, compound

Participants

Reaction Steps

A mixture of 10.0 g (28.2 mmol) of tert.butyl (S)-8-amino-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate, 2.6 g (11.1 mmol) of a tetraethyl orthotitanate and 60 ml of cyclohexanol is stirred at 130° for 24 hours, a small amount of solvent being distilled off three times in vacuo. The mixture is subsequently evaporated in vacuo, the residue is taken up in 60 ml of chloroform, the chloroform solution is treated with water, stirred for a further 1 hour, filtered over siliceous earth and then the organic phase is separated. The organic phase is dried over magnesium sulphate and evaporated. The residue is chromatographed on silica gel while eluting with ethyl acetate and subsequently recrystallized from ethyl acetate. There is obtained cyclohexyl (S)-8-amino-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate of melting point 211°-212°.

Provenance & Evidence