Reacción #1712

Ecuación de reacción

N-chlorocarbonyl-1,2,3,4,4a,9a-hexahydrocarbazole

THF

1-Butyl-4-piperidinylmethanol

THF

methyllithium

→

title compound

N-Carboxy-[1-butyl-4-piperidinylmethyl]-1,2,3,4,4a,9a-hexahydrocarbazole

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGwith stirring
2. 2
   workup.WAITAfter 48 hours
3. 3
   Filtraciónthe reaction mixture was filtered
4. 4
   Otrothe filtrate evaporated under reduced pressure
5. 5
   OtroThe residue was purified by silica-gel chromatography
6. 6
   Lavadoeluting with 2% MeOH/CHCl3 -3%MeOH/CHCl3

Procedimiento

1-Butyl-4-piperidinylmethanol (0.500 g 2.12 mmol) was dissolved in dry THF (3 ml) and treated with methyllithium (1.5M solution in diethyl ether) 2.16 ml, 2.33 mmol) with stirring under nitrogen. After 10 minutes, N-chlorocarbonyl-1,2,3,4,4a,9a-hexahydrocarbazole (0.630 g, 2.68 mmol) (Ref: WO 89/09217) in dry THF (5 ml) was added dropwise with stirring. After 48 hours, the reaction mixture was filtered and the filtrate evaporated under reduced pressure. The residue was purified by silica-gel chromatography, eluting with 2% MeOH/CHCl3 -3%MeOH/CHCl3 to give the title compound as a clear, colourless oil, which was converted to the oxalate salt, nap 187°-189° C.

Fuente