Methyl 3-bromoprop-2-ynoate → 7-Tert-butyl 2-methyl 3-bromo-7-azabicyclo[2.2.1]hepta-2,5-diene-2,7-dicarboxylate
Reaktionsgleichung
[Br:1][C:2]#[C:3][C:4]([O:6][CH3:7])=[O:5].[N:8]1([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9]1>>[Br:1][C:2]1[CH:9]2[N:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:12]([CH:11]=[CH:10]2)[C:3]=1[C:4]([O:6][CH3:7])=[O:5]Komponenten
3
Reaktionsbedingungen
- Temperatur
- 95 °C
Versuchsvorschrift
Into a 2000-mL 3-necked round-bottom flask was placed methyl 3-bromopropiolate (120 g, 736.33 mmol, 1.00 equiv) and tert-butyl 1H-pyrrole-1-carboxylate (615.61 g, 3.68 mol, 5.00 equiv). The resulting solution was stirred for 30 hr at 95° C. in an oil bath. The reaction mixture was cooled and distilled under reduced pressure (20 mm Hg). The fraction collected at 55° C. was purified by silica gel chromatography (ethyl acetate/petroleum ether, 1:20) to afford 7-tert-butyl 2-methyl 3-bromo-7-azabicyclo[2.2.1]hepta-2,5-diene-2,7-dicarboxylate as a yellow liquid.