Sodium triacetoxyborohydride → methyl 3-[4-(7-chloro-2-(methylsulfanyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-yl)piperazin-1-yl]-2,2-dimethylpropanoate

Participants

Reaction Steps

Add methyl 2,2-dimethyl-3-oxo-propanoate (0.928 g, 7.13 mmoles) in DCM (5 mL) to 7-chloro-2-(methylsulfanyl)-11-(piperazin-1-yl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine (1.0 g, 2.85 mmoles) in DCM (10 mL) and stir under nitrogen for 30 minutes at room temperature. Add sodium triacetoxyborohydride (3 equiv; 1.89 g, 8.56 mmoles) to the reaction mixture and stir under nitrogen overnight at room temperature. Add methanol and apply to an SCX-2 column, wash with methanol and elute with 2M ammonia in methanol. Evaporate the methanol solution to give methyl 3-[4-(7-chloro-2-(methylsulfanyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-yl)piperazin-1-yl]-2,2-dimethylpropanoate (1.23 g, 84%). MS (m/z): 461.12 (M+1).

Provenance & Evidence