反应详情

Ethyl [2-(7-[2-methoxy-1-(methoxymethyl)ethoxy]-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]acetate (220 mg) was dissolved in a mixture of tetrahydrofuran (2 mL) and methanol (1 mL). Lithium borohydride (41 mg) was added to the mixture at 0° C. and the mixture was stirred at room temperature for 6.5 h. Water was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (methanol/ethyl acetate/hexane=0/40/60 to 15/85/0, volume ratio) to give an orange oil. The oil was crystallized from acetonitrile. The crystals were recrystallized from acetonitrile-diethyl ether to give the title compound (105 mg, 75%) as colorless crystals. MS 536 (MH+). mp 69-71° C.

1. extractionthe mixture was extracted with ethyl acetate
2. washThe organic layer was washed with saturated brine
3. dry with materialdried over magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated
6. customThe residue was purified by silica gel column chromatography (methanol/ethyl acetate/hexane=0/40/60 to 15/85/0, volume ratio)
7. customto give an orange oil
8. customThe oil was crystallized from acetonitrile
9. customThe crystals were recrystallized from acetonitrile-diethyl ether