Water → HCID 57758728, compound

To a solution of (3R,4S)-3-ethoxycarbonyl-4-fluoromethyl-3-methyl-1-[(1R)-1-phenylethyl]-2-pyrrolidone (1.05 g, 3.42 mmol) in ethanol (20 mL), 10 mol/l aqueous solution of sodium hydroxide (3.42 mL, 34.2 mmol) was added dropwise in an ice bath, and the mixture was stirred for 30 minutes. Water (20 mL) was added to the reaction mixture in an ice bath, and the aqueous solution was washed with diethylether (50 mL). To the aqueous layer was added concentrated hydrochloric acid to pH 2 to 3 in an ice bath, and the solution was extracted with chloroform (50 mL×3). The organic layer was washed with saturated aqueous solution of sodium chloride (50 mL), and dried with anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The concentrate was azeotropically distilled by adding toluene (20 mL), and dried under reduced pressure to obtain 950 mg (99%) of the title compound as a colorless oily substance.

1. washthe aqueous solution was washed with diethylether (50 mL)
2. additionTo the aqueous layer was added concentrated hydrochloric acid to pH 2 to 3 in an ice bath
3. extractionthe solution was extracted with chloroform (50 mL×3)
4. washThe organic layer was washed with saturated aqueous solution of sodium chloride (50 mL)
5. dry with materialdried with anhydrous sodium sulfate
6. filtrationAfter filtration
7. concentrationthe filtrate was concentrated under reduced pressure
8. distillationThe concentrate was azeotropically distilled
9. additionby adding toluene (20 mL)
10. customdried under reduced pressure

ORD record

ord-4f0c1b070f32473db156d2dddb9debfa

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08211910B2