HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 2-[(R)-2-(5-chloro-7-cyclopentylamino-1H-indol-2-yl)-4,5-dihydro-thiazol-4-yl]-ethanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | [(R)-2-(5-chloro-7-cyclopentylamino-1H-indol-2-yl)-4,5-dihydro-thiazol-4-yl]acetic acid methyl ester | HCID 25196144 | — |
| Reactant | lithium borohydride THF | HCID 131718764 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2-[(R)-2-(5-chloro-7-cyclopentylamino-1H-indol-2-yl)-4,5-dihydro-thiazol-4-yl]-ethanol | HCID 25196146 | 100.1% |
Reaction Steps
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%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08309586B2 |
| Source dataset | uspto-grants-2012_11 |
| ORD ID | ord-317d5deb2dfa4603a880361197727009 |
| Source note | uspto-grants-2012_11 |