Hydrochloric Acid → ethyl (2RS,3RS)-3-(4-fluorophenyl)-2-((3-fluoro-4-(trifluoromethyl)phenyl)methyl)-3-hydroxypropionate

To a solution of zinc chloride (7.06 g, 51.8 mmol) in diethyl ether (100 ml) was added sodium borohydride (3.92 g, 103.5 mmol) and the mixture was stirred at room temperature for 30 min. The insoluble material was filtered off. To the filtrate was added a solution of ethyl 3-(4-fluorophenyl)-2-((3-fluoro-4-(trifluoromethyl)phenyl)methyl)-3-oxopropionate (10 g, 25.9 mmol) in diethyl ether (50 ml) and the mixture was stirred at room temperature for 30 min. 1N Hydrochloric acid was added to the reaction solution under ice-cooling for quenching, water (200 ml) was added, and the mixture was extracted with ethyl acetate (300 ml×2). The extract was ashed with water and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to give ethyl (2RS,3RS)-3-(4-fluorophenyl)-2-((3-fluoro-4-(trifluoromethyl)phenyl)methyl)-3-hydroxypropionate (10.0 g, 99%) as a colorless oil.

1. filtrationThe insoluble material was filtered off
2. stirringthe mixture was stirred at room temperature for 30 min
3. temperaturecooling
4. customfor quenching
5. additionwater (200 ml) was added
6. extractionthe mixture was extracted with ethyl acetate (300 ml×2)
7. dry with materialdried over anhydrous magnesium sulfate
8. customevaporated under reduced pressure
9. customThe residue was purified by silica gel column chromatography (ethyl acetate)

ORD record

ord-0cc571c10d4d468ab25cf392d0e7c1c9

Source dataset

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06982348B2