Water → 2-(2-{5-[4-(Methylsulfonyl)phenoxy]-7-(tetrahydro-2H-pyran-4-ylmethoxy)-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)ethanol

Ethyl (2-{5-[4-(methylsulfonyl)phenoxy]-7-(tetrahydro-2H-pyran-4-ylmethoxy)-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetate (310 mg) was dissolved in tetrahydrofuran (15 mL), lithium borohydride (24 mg) was added under ice-cooling, and the mixture was stirred at room temperature for 2.5 hr, and then at 50° C. for 2.5 hr. Lithium borohydride (24 mg) was added to the reaction mixture, and the mixture was stirred at 50° C. for 30 hr. Water was added to the reaction mixture, and the mixture was subjected to extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtrated, and concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography (ethyl acetate:hexane=20:80 to 100:0, volume ratio), and the obtained amorphous solid was washed with diethyl ether to give the title compound (123 mg, yield 55%) as a pale-yellow solid. melting point 104-105° C. MS 531 (MH+).

1. temperaturecooling
2. waitat 50° C. for 2.5 hr
3. stirringthe mixture was stirred at 50° C. for 30 hr
4. extractionthe mixture was subjected to extraction with ethyl acetate
5. washThe organic layer was washed with saturated brine
6. dry with materialdried over magnesium sulfate
7. filtrationfiltrated
8. concentrationconcentrated under reduced pressure
9. washthe obtained amorphous solid was washed with diethyl ether

ORDレコード

ord-8f2730814c8448f695911c88606c6069

出典データセット

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08673942B2