Reaktion #51853

Reaktionsgleichung

water

thiophenol

N-allyl-2-nitro-N-(2-oxo-1-(S)-phenyl-2-pyrrolidin-1-yl-ethyl)-benzenesulfonamide

potassium carbonate

→

title compound

Ausbeute 84.9%

2-Allylamino-2-(S)-phenyl-1-pyrrolidin-1-yl-ethanone

Ausbeute 84.9%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was stirred for 16 hours at ambient temperature
2. 2
   Extraktionextracted with ethyl acetate (3×500 cm3)
3. 3
   WaschenThe combined ethyl acetate extracts were washed with water (2×400 cm3), brine (1×300 cm3)
4. 4
   Trocknendried over sodium sulfate, vacuum
5. 5
   Filtrationfiltered
6. 6
   Sonstigethe volatile fractions removed in vacuo to a foul smelling yellow oil
7. 7
   SonstigeThe crude product was purified by column chromatography (silica
8. 8
   Wascheneluting with hexane-ethyl acetate 1:1 to 0:1

Vorschrift

To a stirred solution of N-allyl-2-nitro-N-(2-oxo-1-(S)-phenyl-2-pyrrolidin-1-yl-ethyl)-benzenesulfonamide (66.2 g, 154 mmol) in anhydrous dimethylformamide (300 cm3) was added potassium carbonate (63.9 g, 462 mmol). The mixture was stirred at ambient temperature for 10 minutes and thiophenol (22.2 cm3, 216 mmol) was added dropwise over 10 minutes. The mixture was stirred for 16 hours at ambient temperature and poured into water (2000 cm3) and extracted with ethyl acetate (3×500 cm3). The combined ethyl acetate extracts were washed with water (2×400 cm3), brine (1×300 cm3), dried over sodium sulfate, vacuum filtered and the volatile fractions removed in vacuo to a foul smelling yellow oil. The crude product was purified by column chromatography (silica, eluting with hexane-ethyl acetate 1:1 to 0:1 and then dichloromethane-methanol 19:1 to 9:1) to afford the title compound as a yellow viscous oil (31.9 g, 84.9%) with a positive ion ESI (M+H)+245.3.

Quelle