Reaktion #83909

Reaktionsgleichung

(2,4-difluorophenyl)[1-(phenylmethyl)-3-pyrrolidinyl]methanone

NH2OH.HCl

ammonium acetate

→

(2,4-difluorophenyl)[1-(phenylmethyl)-3-pyrrolidinyl]methanone oxime

Ausbeute 52.0%

Lösungsmittel

ethanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe resulting mixture was refluxed for 3.5 hours
2. 2
   EinengenThe reaction mixture was concentrated
3. 3
   Sonstigeto remove ethanol
4. 4
   workup.ADDITIONpoured into water (500 ml)
5. 5
   Extraktionextracted with dichloromethane (500 ml)
6. 6
   Waschenby washing with water, brine
7. 7
   Trocknendrying over magnesium sulfate
8. 8
   EinengenThe product was concentrated to an oil
9. 9
   Sonstigepurified by column chromatography

Vorschrift

To the compound (2,4-difluorophenyl)[1-(phenylmethyl)-3-pyrrolidinyl]methanone (22 g) in 95% ethanol (350 ml) and water (100 ml) was added NH2OH.HCl (10.1 g) and ammonium acetate (12.7 g, 2.1 eq). The resulting mixture was refluxed for 3.5 hours. The mixture was then allowed to stir at room temperature for 24 hours. The reaction mixture was concentrated to remove ethanol, poured into water (500 ml), and extracted with dichloromethane (500 ml). This was followed by washing with water, brine, and drying over magnesium sulfate. The product was concentrated to an oil and purified by column chromatography to yield 12 g of (2,4-difluorophenyl)[1-(phenylmethyl)-3-pyrrolidinyl]methanone oxime.

Quelle