Reacción #159294

Ecuación de reacción

1-tert-butyl 2-methyl (2S,4S)-4-hydroxypyrrolidine-1,2-dicarboxylate

3-chloroquinoxalin-2-ol

Acetyl Chloride

Quinoxaline 1,4-Dioxide

PPh3

DIAD

Quinoxaline

→

title compound

Rendimiento 77.0%

1-tert-butyl 2-methyl (2S,4R)-4-[(3-chloroquinoxalin-2-yl)oxy]pyrrolidine-1,2-dicarboxylate

Rendimiento 77.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter evaporation of the volatiles
2. 2
   Otrothe residue was purified on SiO2 (gradient elution, 0-70% EtOAc/petroleum ether)

Procedimiento

A solution of 3-chloroquinoxalin-2-ol (1.44 g, 7.97 mmol) (Yusuf Ahmad et al., Quinoxaline Derivatives, XI. The Reaction of Quinoxaline 1,4-Dioxide and Some of Its Derivatives with Acetyl Chloride, 38(12) J. ORG. CHEM. 2176 (1973)) and 1-tert-butyl 2-methyl (2S,4S)-4-hydroxypyrrolidine-1,2-dicarboxylate (2.05 g, 8.37 mmol) in THF (190 ml) was cooled to 0° C., then treated with PPh3 (2.51 g, 9.57 mmol). DIAD (1.86 ml, 9.57 mmol) was added dropwise, and the mixture was stirred at 20° C. for 1 hour. After evaporation of the volatiles, the residue was purified on SiO2 (gradient elution, 0-70% EtOAc/petroleum ether) to afford the title compound (2.5 g, 77%). LCMS (ES+) m/z 408 (M+H)+

Fuente