Reacción #1851989

Ecuación de reacción

potassium hydroxide

ethyl (6bR, 10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate

→

title compound

Rendimiento 95.1%

(6bR,10aS)-3-methyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline

Rendimiento 95.1%

Disolventes

1-butanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe resulting mixture was heated
2. 2
   Temperaturaunder reflux for 5 h
3. 3
   OtroIt was then evaporated under reduced pressure
4. 4
   workup.ADDITIONthe residue treated with water
5. 5
   Extracciónextracted with dichloromethane (2×)
6. 6
   LavadoThe extract was washed with water
7. 7
   Secadodried over magnesium sulfate
8. 8
   Concentraciónconcentrated

Procedimiento

Powdered potassium hydroxide (10.0 g) was added to a stirred solution of ethyl (6bR, 10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate (4.52 g, 15.0 mmol) in warm 1-butanol (50 mL) and the resulting mixture was heated under reflux for 5 h. It was then evaporated under reduced pressure and the residue treated with water and extracted with dichloromethane (2×). The extract was washed with water, dried over magnesium sulfate and concentrated to yield 3.27 g (95%) of the title compound as a viscous liquid. 1H NMR (CDCl3, 300 MHz) δ 1.74-1.93 (m, 4H), 2.57-2.71 (m, 1H), 2.80-2.95 (m, 3H), 2.87 (s, 3H), 2.95-3.12 (m, 2H), 3.26-3.38 (m, 3H), 3.55-3.64 (m, 1H), 6.41 (d, J=7.3 Hz, 1H), 6.51 (d, J=7.3 Hz, 1H), 6.65 (t, J=7.3 Hz, 1H) ppm. MS (CI): 230 (M+H+)

Fuente