Sodium Hydroxide → (4S)-1-tert-Butoxycarbonyl-4-fluoro-L-proline

Methyl(2S,4S)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylate (5.00 g) was dissolved in methanol (30 mL). While stirring this solution under ice cooling, 5 mol/L aqueous sodium hydroxide (12 mL) was gradually added dropwise. After stirring at room temperature for 2 hours, the reaction mixture was evaporated under reduced pressure to remove methanol. The resulting residue was washed with diethyl ether, diluted with 10% aqueous potassium bisulfate (70 mL), and then extracted with ethyl acetate. The extracted solution was washed with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. Diisopropyl ether (20 mL) was added to the resulting residue and the precipitated crystal was collected by filtration to give the titled compound (3.91 g, white powder).

1. stirringAfter stirring at room temperature for 2 hours
2. customthe reaction mixture was evaporated under reduced pressure
3. customto remove methanol
4. washThe resulting residue was washed with diethyl ether
5. additiondiluted with 10% aqueous potassium bisulfate (70 mL)
6. extractionextracted with ethyl acetate
7. washThe extracted solution was washed with water and saturated aqueous sodium chloride
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated under reduced pressure
10. additionDiisopropyl ether (20 mL) was added to the resulting residue
11. filtrationthe precipitated crystal was collected by filtration

ORD record

ord-1b27ab8b3ccd4a708bd1b5d76f061352

Source dataset

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07279584B2