Ethyl Acetate → HCID 178487963, compound

Participants

Reaction Steps

Sodium borohydride (86 mg, 2.28 mmol, 10.0 eq) is added at 0° C. to a stirred suspension of [trans-4-(6-methoxy-2-oxo-2H-1-oxa-9-aza-phenanthren-3-ylmethyl)-cyclohexyl]-carbamic acid tert-butyl ester (100 mg, 0.23 mmol, 1.0 eq) in methanol (10 mL). After 8 hours stirring at room temperature, the reaction mixture is quenched with ammonium chloride aqueous solution (10 mL), methanol is removed and the resulting residue is extracted with ethyl acetate (3×20 mL) and brine (20 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a crude product that is purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate, 2:1, v/v) to afford {trans-4-[3-hydroxy-2-(3-hydroxy-6-methoxy-quinolin-4-ylmethyl)-propyl]-cyclohexyl}-carbamic acid tert-butyl ester as a white solid (60 mg, 59% yield).

Provenance & Evidence