Sodium borohydride → [5-(1-cyclohexylmethyl-7-methoxy-1H-indol-3-yl)thiazol-2-yl]-methanol

Participants

Reaction Steps

To a solution of 5-(1-cyclohexylmethyl-7-methoxy-1H-indol-3-yl)thiazole-2-carboxylic acid methyl ester (418 mg, 1.09 mmol) in methanol (10 ml) and tetrahydrofuran (10 ml) was added sodium borohydride (83 mg, 2.18 mmol) portionwise over 2 minutes. The reaction was stirred for a further 1 h and then quenched with aqueous hydrochloric acid (1M; 10 ml). The mixture was poured into a separating funnel, diluted with dichloromethane (50 ml) and washed with water (20 ml). The combined organic layers were dried, filtered and the solvent removed in vacuo to leave a yellow oil. The oil was purified by flash column chromatography using 50-100% (v/v) diethyl ether in heptane to give [5-(1-cyclohexylmethyl-7-methoxy-1H-indol-3-yl)thiazol-2-yl]-methanol (308 mg, 0.86 mmol) as an off-white foam.

Provenance & Evidence