Reacción #83623

Ecuación de reacción

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

→

isoxazole indole

Rendimiento 30.9%

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

Rendimiento 30.9%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas sonicated at 50-55 KHz for 2 hr
2. 2
   TemperaturaThe reaction mixture 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 residue was chromatographed (flash column, silica gel, ethyl acetate)

Procedimiento

A mixture of (+)(2aS,4R)-6-(3-isoxazolyl)-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole (180 mg, 0.5 mmol) and 1 g of MnO2 in 40 mL of CH2Cl2 was sonicated at 50-55 KHz for 2 hr. The reaction mixture warmed to reflux during the time period. The reaction mixture was filtered through a celite pad and the filtrate was concentrated to dryness in vacuo. The residue was chromatographed (flash column, silica gel, ethyl acetate) to provide 50 mg of the isoxazole indole product as an oil. MS (FD) 323

Fuente