Trifluoroacetic acid → HCID 68861909, compound

To a solution of tert-butyl (3S)-1-benzyloxycarbonyl-4-fluoro-3-methylpyrrolidine-3-carboxylate (isomer A) (1.80 g, 5.33 mmol) in dichloromethane (10 mL), trifluoroacetic acid (10 mL) was added dropwise and, and the mixture was stirred for 2 hours. The reaction mixture was concentrated under reduced pressure, and saturated aqueous solution of sodium hydrogencarbonate (30 mL) was added to the concentrate under reduced pressure. The aqueous solution was washed with diethylether (50 mL), and to the aqueous layer was added 1 mol/l hydrochloric acid to pH 2 to 3, and the mixture was extracted with chloroform (200 mL×2). The organic layer was dried with anhydrous sodium sulfate, and 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 1.86 g (quantitative) of the title compound (isomer A) as a colorless oily substance.

1. concentrationThe reaction mixture was concentrated under reduced pressure, and saturated aqueous solution of sodium hydrogencarbonate (30 mL)
2. additionwas added to the
3. concentrationconcentrate under reduced pressure
4. washThe aqueous solution was washed with diethylether (50 mL)
5. additionto the aqueous layer was added 1 mol/l hydrochloric acid to pH 2 to 3
6. extractionthe mixture was extracted with chloroform (200 mL×2)
7. dry with materialThe organic layer was dried with anhydrous sodium sulfate
8. filtrationafter filtration
9. concentrationthe filtrate was concentrated under reduced pressure
10. distillationThe concentrate was azeotropically distilled
11. additionby adding toluene (20 mL)
12. customdried under reduced pressure

ORD record

ord-3c8fdcf42fac4d128d0c100043276b39

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476429B2