Water → 2-[(R)-2-(5-chloro-7-cyclopentylamino-1H-indol-2-yl)-4,5-dihydro-thiazol-4-yl]-ethanol

The compound (550 mg, 1.4 mmol) prepared in Example 26 was dissolved in tetrahydrofuran (50 ml). 1 M lithium borohydride tetrahydrofuran solution (2.11 ml, 2.11 mmol) was added thereto, and the mixture was stirred for 1 h while raising the reaction temperature from −60° C. to 0° C. After completion of the reaction, water was added. The mixture was extracted with ethyl acetate, washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The filtrate was distilled under reduced pressure, and separated by column chromatography to give the title compound (510 mg, Yield 100%).

1. temperaturewhile raising the reaction temperature from −60° C. to 0° C
2. additionwas added
3. extractionThe mixture was extracted with ethyl acetate
4. washwashed with saturated sodium chloride solution
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltered
7. distillationThe filtrate was distilled under reduced pressure
8. customseparated by column chromatography

ORD record

ord-317d5deb2dfa4603a880361197727009

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08309586B2