反应详情

温度

-78 °C

A stirred solution of tert-butyl 3-benzoylpiperidine-1-carboxylate (160 mg, 0.55 mmol) in dry THF (2 mL) was cooled to −70° C. and 4-pentenylmagnesium bromide in THF (1.8 mL of −2.5 M, 2.8 mmol) was added dropwise. The mixture was stirred at −78° C. and allowed to warm to rt overnight. The reaction was quenched with satd aq ammonium chloride. The aqueous layer was extracted with Et2O (3×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated to dryness. The crude material was purified by flash chromatography on a prepacked silica cartridge eluted with an EtOAc/hexanes gradient. tert-Butyl 3-((R)-1-hydroxy-1-phenylhex-5-enyl)piperidine-1-carboxylate (174 mg, 88%) was isolated as an oil. MS ESI +ve m/z 382 (M+Na)+.

1. temperatureto warm to rt overnight
2. customThe reaction was quenched with satd aq ammonium chloride
3. extractionThe aqueous layer was extracted with Et2O (3×)
4. washThe combined organic layers were washed with brine
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. customevaporated to dryness
8. customThe crude material was purified by flash chromatography on a prepacked silica cartridge
9. washeluted with an EtOAc/hexanes gradient