Reacción #58778

Ecuación de reacción

2′,3′,5′-triacetoxy-2,6-dichloroadenosine

cyclopentylamine

ethanol

→

2-chloro-N6-cyclopentyladenosine

Disolventes

ethyl acetate

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe resulting solution was heated
2. 2
   Temperaturaat reflux for about 15 hours
3. 3
   Concentraciónconcentrated in vacuo
4. 4
   Otroto provide a crude residue which
5. 5
   Otrotransferred to a separatory funnel
6. 6
   OtroThe organic layer was separated
7. 7
   Secadodried over sodium sulfate
8. 8
   Concentraciónconcentrated in vacuo
9. 9
   Otroto provide a crude residue which
10. 10
    Otrowas purified

Procedimiento

2′,3′,5′-triacetoxy-2,6-dichloroadenosine (1.5 g) and cyclopentylamine (8 eq.) were diluted with ethanol (50 eq.) and the resulting solution was heated at reflux for about 15 hours, then cooled to room temperature and concentrated in vacuo to provide a crude residue which was diluted with a mixture of ethyl acetate and water and transferred to a separatory funnel. The organic layer was separated, dried over sodium sulfate and concentrated in vacuo to provide a crude residue which was purified using flash column chromatography on silica gel (8% MeOH-dichloromethane as eluent) to provide 2-chloro-N6-cyclopentyladenosine (0.948 g). MS m/z 370.32 [M+H]+.

Fuente