Trifluoroacetic acid → HCID 68861909, compound

To a solution of tert-butyl (3S)-1-benzyloxycarbonyl-4-fluoro-3-methylpyrrolidine-3-carboxylate isomer B (1.35 g, 4.00 mmol) in dichloromethane (7 mL), trifluoroacetic acid (7 mL) was added dropwise in an ice bath, and the mixture was stirred for 2 hours. After concentrating the reaction mixture under reduced pressure, saturated aqueous solution of sodium hydrogencarbonate (30 mL) was added to the concentrate in an ice bath, and the aqueous solution was washed with diethylether (50 mL). To the aqueous layer was added 1 mol/l hydrochloric acid to pH 2 to 3, and the solution was extracted with chloroform (150 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 1.25 g (quantitative) of the title compound (isomer B) as a colorless oily substance.

1. concentrationAfter concentrating the reaction mixture under reduced pressure, saturated aqueous solution of sodium hydrogencarbonate (30 mL)
2. additionwas added to the
3. concentrationconcentrate in an ice bath
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 solution was extracted with chloroform (150 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-5f89d3bcc12c40fdbbdfc04bd6b4ea3f

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08211910B2