Reacción #517961

Ecuación de reacción

hydrochloric acid

Borane-trimethylamine complex

hydrochloric acid

4-methoxyindole

→

desired compound

Rendimiento 83.0%

4-methoxyindoline

Rendimiento 83.0%

Disolventes

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture was heated
2. 2
   Temperaturato reflux for 30 minutes
3. 3
   Temperaturathe mixture was heated
4. 4
   Temperaturato reflux for 15 minutes
5. 5
   OtroThe solvent was removed under reduced pressure and 1N aqueous sodium hydroxide solution
6. 6
   workup.ADDITIONwas added
7. 7
   Extracciónby extracting the aqueous layer with ether (3×20 ml)
8. 8
   LavadoThe obtained organic layers were washed with saturated brine
9. 9
   Secadodried over sodium sulfate
10. 10
    OtroAfter removing solids
11. 11
    Filtraciónby filtration
12. 12
    Otrothe solvent was removed under reduced pressure
13. 13
    Otrothe obtained crude product
14. 14
    Otrowas purified by silica gel column chromatography

Procedimiento

Borane-trimethylamine complex (3.00 g) and 10.5N hydrochloric acid (2.25 ml) were added to 4-methoxyindole (1.29 g) in dioxane (20 ml), and the mixture was heated to reflux for 30 minutes. To this mixture, 6N hydrochloric acid (7.00 ml) was added and the mixture was heated to reflux for 15 minutes. The solvent was removed under reduced pressure and 1N aqueous sodium hydroxide solution was added to change the aqueous layer to alkaline condition, followed by extracting the aqueous layer with ether (3×20 ml). The obtained organic layers were washed with saturated brine and dried over sodium sulfate. After removing solids by filtration, the solvent was removed under reduced pressure, and the obtained crude product was purified by silica gel column chromatography to obtain the desired compound (1.08 g, yield: 83%).

Fuente