Reacción #42520

Ecuación de reacción

methyl 1,2,3,4-tetrahydroquinoline-7-carboxylate

cesium bicarbonate

n-butyl bromide

→

methyl 1-butyl-1,2,3,4-tetrahydroquinoline-7-carboxylate

Rendimiento 67.1%

Disolventes

THF

EtOAc

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction mixture was heated
2. 2
   Temperaturaat reflux for 48 h
3. 3
   LavadoThe organic layer was washed with water, and brine
4. 4
   Secadodried (magnesium sulfate)
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated under reduced pressure
7. 7
   OtroPurification by flash column chromatography (silica, 1:3 ethyl acetate/hexanes)

Procedimiento

To a stirred solution of methyl 1,2,3,4-tetrahydroquinoline-7-carboxylate (180 mg, 0.94 mmol) and cesium bicarbonate (1.5 g, 4.7 mmol) in THF (2 mL) was added n-butyl bromide (1.0 mL, 9.4 mmol), and the reaction mixture was heated at reflux for 48 h. The reaction mixture was cooled to room temperature, and diluted with EtOAc. The organic layer was washed with water, and brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 1:3 ethyl acetate/hexanes) afforded methyl 1-butyl-1,2,3,4-tetrahydroquinoline-7-carboxylate (156 mg): ESI MS m/z 248 [M+H]+.

Fuente