Sodium borohydride → [(S)-2-(7-Hydroxymethyl-furo[2,3-g]indazol-1-yl)-1-methylethyl]-carbamic acid benzyl ester

Participants

Reaction Steps

To a stirred solution of the product from Step A (0.13 g, 0.27 mmol) in ethanol (10 mL) was added calcium chloride (0.06 g, 0.54 mmol) in THF (2 mL) followed by sodium borohydride (0.04 g, 1.07 mmol) at 0° C. and the mixture was stirred at room temperature for 20 h. The reaction mixture was evaporated to a residue and a saturated aqueous solution of ammonium chloride (20 mL was added followed by ethyl acetate (50 mL). The organic layer was separated and the aqueous was extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine (30 mL), dried and evaporated to a residue, which was purified by chromatography (silica, 50% ethyl acetate in hexane) to give an oil (0.05 g, 49%); MS (ES) m/z 380 (M+).

Provenance & Evidence