反应详情

温度

-78 °C

n-BuLi (600 mL, 1.5 mol) was added dropwise to a solution of TMSCHN2 (690 mL, 1.38 mol) in dry THF (3 L) at −78° C., and the mixture was stirred at −78° C. for 30 minutes. The mixture was then transferred to a solution of (S)-1-tert-butyl 2-ethyl 5-oxopyrrolidine-1,2-dicarboxylate (300 g, 1.17 mol) in dry THF (3 L) via cannula, and the mixture was stirred at −78° C. for 30 minutes. The reaction mixture was then quenched with sat. NH4Cl solution, and extracted with DCM (3×). The combined organic layer was concentrated under reduced pressure and the crude product was purified by silica gel column chromatography (3:1 petroleum ether/EtOAc) to afford (S)-ethyl 2-((tert-butoxycarbonyl)amino)-6-diazo-5-oxohexanoate (262 g, 75%) as a yellow solid.

1. stirringthe mixture was stirred at −78° C. for 30 minutes
2. customThe reaction mixture was then quenched with sat. NH4Cl solution
3. extractionextracted with DCM (3×)
4. concentrationThe combined organic layer was concentrated under reduced pressure
5. customthe crude product was purified by silica gel column chromatography (3:1 petroleum ether/EtOAc)