Reacción #83624

Ecuación de reacción

(-)(2aR,4S)-6-(3-isoxazolyl)-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole

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title product

Rendimiento 14.2%

(-)(4R)-6-(3-isoxazolyl)-4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[cd]indole

Rendimiento 14.2%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas sonicated at 50-55 KHz for four hours
2. 2
   TemperaturaThe reaction mixture was warmed
3. 3
   Temperaturato reflux during the time period
4. 4
   Filtraciónthe reaction mixture was filtered through a celite pad
5. 5
   Concentraciónthe filtrate was concentrated to dryness in vacuo
6. 6
   OtroThe resulting residue was chromatographed (flash column, silica gel, EtOAc)

Procedimiento

A mixture of (-)(2aR,4S)-6-(3-isoxazolyl)-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole (400 mg, 1.2 mmol) and 1 g of MnO2 in 100 ml of CH2Cl2 was sonicated at 50-55 KHz for four hours. The reaction mixture was warmed to reflux during the time period. After four hours, the reaction mixture was filtered through a celite pad and the filtrate was concentrated to dryness in vacuo. The resulting residue was chromatographed (flash column, silica gel, EtOAc) to provide 55 mg of title product as an oil. MS m/e 323 (FD)

Fuente