反应详情

温度

-70 °C

A stirred solution of tert-butyl 3-benzoylpyrrolidine-1-carboxylate (489 mg, 1.78 mmol) in dry THF (10 mL) was cooled to −70° C. and 2 M 4-methoxybutylmagnesium chloride in THF (8 mL, 16 mmol) was added. The mixture was stirred at −70° C. for 1 h and poured into satd aq NH4Cl (100 mL). The mixture was extracted with ether (2×100 mL) and the combined ether extracts were dried over Na2SO4. Removal of the solvent left an oil which was purified by flash chromatography on a 40-g silica cartridge eluted with a 0 to 100% ethyl acetate in hexanes gradient to afford tert-butyl 3-(1-hydroxy-5-methoxy-1-phenylpentyl)pyrrolidine-1-carboxylate (290 mg, 44%).

1. extractionThe mixture was extracted with ether (2×100 mL)
2. dry with materialthe combined ether extracts were dried over Na2SO4
3. customRemoval of the solvent
4. waitleft an oil which
5. customwas purified by flash chromatography on a 40-g silica cartridge
6. washeluted with a 0 to 100% ethyl acetate in hexanes gradient