Reacción #51854

Ecuación de reacción

triethylamine

2-Chloro-1-methylpyridinium iodide

allyl-(1-(S)-phenyl-2-pyrrolidin-1-yl-ethyl)-amine

2-[3-(pyrrolidine-1-sulfonyl)-phenyl]-pent-4-enoic acid

→

title compound

Rendimiento 92.9%

2-[3-(Pyrrolidine-1-sulfonyl)-phenyl]-pent-4-enoic acid allyl-(1-(S)-phenyl-2-pyrrolidin-1-yl-ethyl)-amide

Rendimiento 92.9%

Disolventes

ethyl acetate

water

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto afford a yellow slurry
2. 2
   Otroto afford a brown solution
3. 3
   ExtracciónThe aqueous was extracted with ethyl acetate (3×30 cm3)
4. 4
   Lavadothe combined ethyl acetate extracts were washed with 1M sodium bicarbonate (2×50 cm3), brine (1×50 cm3)
5. 5
   Secadodried over sodium sulfate, vacuum
6. 6
   Filtraciónfiltered
7. 7
   Otrothe volatile fractions removed in vacuo to a crude brown oil
8. 8
   OtroThe crude product was purified by column chromatography (silica
9. 9
   Lavadoeluting with dichloromethane-methanol 99:1 to 95:5

Procedimiento

To a stirred solution of allyl-(1-(S)-phenyl-2-pyrrolidin-1-yl-ethyl)-amine (1.00 g, 4.34 mmol) in dichloromethane (22 cm3) at ambient temperature was added 2-[3-(pyrrolidine-1-sulfonyl)-phenyl]-pent-4-enoic acid (1.34 g, 4.34 mmol) followed by 2-Chloro-1-methylpyridinium iodide (2.22 g, 8.68 mmol) and triethylamine (1.82 cm3, 13.0 mmol) to afford a yellow slurry. The mixture was stirred at ambient temperature for 44 hours to afford a brown solution. The solution was diluted with ethyl acetate (50 cm3) and poured into water (100 cm3). The aqueous was extracted with ethyl acetate (3×30 cm3) and the combined ethyl acetate extracts were washed with 1M sodium bicarbonate (2×50 cm3), brine (1×50 cm3), dried over sodium sulfate, vacuum filtered and the volatile fractions removed in vacuo to a crude brown oil. The crude product was purified by column chromatography (silica, eluting with dichloromethane-methanol 99:1 to 95:5 to afford the title compound as a tan viscous oil (2.10, 92.9%) with a positive ion ESI (M+H)+522.3.

Fuente