Reacción #42478

Ecuación de reacción

methyl 4-butyl-3-oxo-1,2,3,4-tetrahydroquinoxaline-6-carboxylate

borane dimethylsulfide

→

title compound

Rendimiento 45.8%

Methyl 4-butyl-1,2,3,4-tetrahydroquinoxaline-6-carboxylate

Rendimiento 45.8%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe resulting mixture was refluxed for 24 h
2. 2
   Otroquenched with methanol
3. 3
   Otrothe solvent was removed under reduced pressure
4. 4
   OtroPurification by flash column chromatography (silica, 1:1 ethyl acetate/hexanes)

Procedimiento

To an ice-cold, stirred solution of methyl 4-butyl-3-oxo-1,2,3,4-tetrahydroquinoxaline-6-carboxylate (840 mg) in tetrahydrofuran (32 mL) was added borane dimethylsulfide complex (3.2 mL, 2.0 M tetrahydrofuran) and the resulting mixture was refluxed for 24 h. The mixture was cooled to room temperature, quenched with methanol, and the solvent was removed under reduced pressure. Purification by flash column chromatography (silica, 1:1 ethyl acetate/hexanes) provided 364 mg of the title compound: 1H NMR (300 MHz, CDCl3) δ 7.27, 7.22, 6.41, 3.84, 3.47-3.45, 3.32-3.23, 1.60-1.58, 1.42-1.37, 0.99-0.94.

Fuente