Hydrochloric Acid → HCID 67118535, compound

Participants

Reaction Steps

Ethyl (2-{7-(2-{[di-tert-butyl(phenyl)silyl]oxy}-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetate (500 mg) was dissolved in tetrahydrofuran (20 mL), lithium borohydride (21 mg) was added under ice-cooling, and the mixture was stirred for 1 hr. Lithium borohydride (28 mg) was added again to the reaction solution, and the mixture was further stirred at room temperature for 1 hr, and then at 50° C. for 7 hr. 1M Hydrochloric acid was added to the reaction mixture, and the mixture was subjected to extraction with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, filtrated, and concentrated under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (ethyl acetate:hexane=20:80 to 70:30, volume ratio) to give the title compound (123 mg, yield 55%) as a yellow oil. MS 729 (MH+).

Provenance & Evidence