Sodium borohydride → HCID 15952180, compound

Participants

Reaction Steps

To a solution of 10-[(2′-acetyl-2-methyl-1,1′-biphenyl-4-yl)carbonyl]-N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide of Example 29 (0.122 g, 0.220 mmol) in 2-propanol (5 mL) and water (1 mL) was added sodium borohydride (0.0092 mg, 0.242 mmol) and the reaction mixture stirred at room temperature under nitrogen for 24 hours. The reaction was quenched by the addition of 2 M hydrochloric acid (10 mL) and then washed with diethyl ether (20 mL). The aqueous phase was basified by the addition of 2 M sodium hydroxide and the resulting milky suspension extracted with ethyl acetate ( 2×30 mL). The combined organic extracts were washed with water (50 mL) and brine (50 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford a colorless syrup. Purification by flash chromatography using a solvent gradient of 1 to 5% methanol in dichloromethane gave a colorless glass that was recrystallized from diethyl ether/hexane to afford the title compound (0.061 g, 50%) as white solid.

Provenance & Evidence