Reaktion #316738

Reaktionsgleichung

(3S)-3-(tert-butoxycarbonylamino)-3-fluoromethyl-4-methyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine

borane

→

title compound

Ausbeute 75.4%

(3S)-3-(tert-Butoxycarbonylamino)-3-fluoromethyl-4-methyl-1-[(1R)-1-phenylethyl]pyrrolidine

Ausbeute 75.4%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenAfter concentrating the reaction mixture under reduced pressure, water (1 mL), ethanol (9 mL), and triethylamine (1 mL)
2. 2
   workup.ADDITIONwere added in an ice bath
3. 3
   Temperaturthe mixture was heated
4. 4
   Temperaturunder reflux for 1.5 hours
5. 5
   EinengenAfter concentrating the reaction mixture under reduced pressure, water (100 mL)
6. 6
   workup.ADDITIONwas added
7. 7
   Extraktionthe mixture was extracted with chloroform (100 mL×2)
8. 8
   WaschenThe organic layer was washed with saturated aqueous solution of sodium chloride (100 mL)
9. 9
   Trocknendried with anhydrous sodium sulfate
10. 10
    FiltrationAfter the filtration
11. 11
    Einengenthe filtrate was concentrated under reduced pressure
12. 12
    Sonstigethe residue was purified by silica gel column chromatography (elusion by hexane ethyl acetate, 12:1→1:1)

Vorschrift

To a solution of (3S)-3-(tert-butoxycarbonylamino)-3-fluoromethyl-4-methyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine (485 mg, 1.38 mmol) in tetrahydrofuran (10 mL), 1.00M solution of borane in tetrahydrofuran (4.57 mL, 4.57 mmol) was added in an ice bath, and the mixture was stirred at room temperature for 15 hours. After concentrating the reaction mixture under reduced pressure, water (1 mL), ethanol (9 mL), and triethylamine (1 mL) were added in an ice bath, and the mixture was heated under reflux for 1.5 hours. After concentrating the reaction mixture under reduced pressure, water (100 mL) was added, and the mixture was extracted with chloroform (100 mL×2). The organic layer was washed with saturated aqueous solution of sodium chloride (100 mL), and dried with anhydrous sodium sulfate. After the filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (elusion by hexane ethyl acetate, 12:1→1:1) to obtain 350 mg (75%) of the title compound as a colorless oily substance.

Quelle