Sodium cyanoborohydride → HCID 69272023, compound

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Reaction Steps

Add sodium cyanoborohydride (3.0 g, 47.6 mmol) to a solution of benzyl-(1H-indol-7-ylmethyl)carbamic acid tert-butyl ester (10.0 g, 29.8 mmol) in acetic acid. Stir the mixture at ambient temperature for 3 hours. Dilute with ethyl acetate and cool in an ice bath. Wash the mixture with aqueous 3.0 N sodium hydroxide until pH is 8. Dry the organic layer with magnesium sulfate and concentrate. Purify by chromatography (silica gel; hexane/ethyl acetate; 3:1 to 0:1) to afford a solid as the title compound (5.0 g, 50%). MS (ESI) m/z 339 (M+H)+.

Provenance & Evidence