反应详情

温度

-5 °C

Dissolve 1-(trans-4-hydroxy-cyclohexyl)-pyrrolidin-2-one (144 g, 0.79 mol) in dry tetrahydrofuran (5 L) and cool to −5° C. under nitrogen. Add triphenylphosphine (310 g, 1.185 mol) and 4-nitrobenzoic acid (198 g, 1.185 mol). Add diisopropyl azodicarboxylate (230 mL, 1.185 mol) drop-wise and stir at room temperature overnight. Add saturated aqueous sodium bicarbonate (1 L) and extract into dichloromethane (2×2.5 L) in a 20 L separating funnel. Dry the combined organic layers over magnesium sulfate, filter and concentrate. Purify over silica gel (iso-hexane/ethyl acetate 50-100% then 10% methanol in ethyl acetate) to afford 163 g (62%) of the title compound.

1. extractionAdd saturated aqueous sodium bicarbonate (1 L) and extract into dichloromethane (2×2.5 L) in a 20 L
2. customseparating funnel
3. dry with materialDry the combined organic layers over magnesium sulfate
4. filtrationfilter
5. concentrationconcentrate
6. customPurify over silica gel (iso-hexane/ethyl acetate 50-100%