反应详情

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.

1. customquenched with aqueous hydrochloric acid (1M; 10 ml)
2. additionThe mixture was poured into a separating funnel
3. additiondiluted with dichloromethane (50 ml)
4. washwashed with water (20 ml)
5. customThe combined organic layers were dried
6. filtrationfiltered
7. customthe solvent removed in vacuo
8. customto leave a yellow oil
9. customThe oil was purified by flash column chromatography