Hydrochloric Acid → (10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[2-chloro-4-(3-hydroxy-2-methyl-cyclohex-1-en-1-yl)-phenyl]-methanone

Participants

Reaction Steps

(10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[2-chloro-4-(2-methyl-3-oxo-cyclohex-1-en-1-yl)-phenyl]-methanone of Example 13 (0.060 g, 0.139 mmol) and cerium(III) chloride (0.034 g, 0.139 mmol) were dissolved in methanol (0.7 mL) followed by addition of solid sodium borohydride (0.0053 g, 0.139 mmol). Gas was vigorously evolved from the reaction mixture for approximately two minutes, after which 0.1 N hydrochloric acid (25 mL) was added. A white precipitate formed which was extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate, concentrated and the residue purified by flash column chromatography on silica gel, eluting with 50% ethyl acetate in hexane. A clear oil was isolated which was dissolved in ether and precipitated with pentane to afford the title compound (0.050 g) as a white solid.

Provenance & Evidence