Sodium Hydroxide → 1-[1-Benzyloxycarbonyl-4-(S)-fluoro-3-(S)-pyrrolidinyl]-cyclopropanecarboxylic acid

Temperature

40 °C

1-Benzyloxycarbonyl-4-(S)-(1-ethoxycarbonylcyclopropyl)-3-(S)-fluoropyrrolidine (4.67 g, 13.92 mmol) was dissolved in ethanol (50 ml), and a 1 N sodium hydroxide aqueous solution (50 ml) was added dropwise to the resulting solution. The reaction solution was stirred at 40° C. for 1.5 hours and then ethanol was evaporated under reduced pressure. The resulting residue was mixed with water (50 ml) and washed with chloroform (100 ml), and the thus separated aqueous layer was acidified by adding dropwise 1 N hydrochloric acid and extracted with chloroform (200 ml×2) and then with diethyl ether (100 ml). The organic layers were combined and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain 3.94 g (92.1%) of the title compound as a colorless amorphous substance.

1. customethanol was evaporated under reduced pressure
2. additionThe resulting residue was mixed with water (50 ml)
3. washwashed with chloroform (100 ml)
4. additionby adding dropwise 1 N hydrochloric acid
5. extractionextracted with chloroform (200 ml×2)
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationAfter filtration
8. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-83f7ae86c001470280f29970e4182334

Source dataset

uspto-grants-2001_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06184388B2