Hydride Reductions of 1H-Pyrrolo[2,1-c][1,4]-benzodiazepine-5,11-diones: Selective Reduction of Secondary Amides to Carbinolamines

Abstract

For the syntheses of radiolabelled pyrrolo[1,4]benzodiazepine antitumour antibiotics we required a method in which the unstable carbinolamine functionality was introduced prior to the radiolabel. In turn this required the selective reduction of a secondary amide in the presence of, inter alia, a tertiary amide. We report methods which can be used to achieve this outcome in a series of 1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-diones.