反应详情

To a suspension of naphthalen-2-ylmethyl 3-fluoro-4-oxopiperidine-1-carboxylate (41.75 g, 138.6 mmol) in anhydrous THF (800 mL) at 0° C. was added L-Selectride (346 mL, 1.0 M, 346 mmol) dropwise over 30 minutes, during which a yellow solution formed. The solution was allowed to warm to ambient temperature and stir for 16 hours. The mixture was cooled to 0° C., then treated with methanol (160 mL) and 2 N NaOH (350 mL) followed by the dropwise addition of 30% H2O2 (160 mL), during which an exotherm was observed. After stirring at 0° C. for an additional 1 hour and then at ambient temperature for 3 hours, the mixture was extracted with EtOAc. The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified on a large silica gel plug eluting with hexanes:EtOAc, 1:1 to afford 26.78 g (64%) of desired product as a solid.

1. customduring which a yellow solution formed
2. temperatureThe mixture was cooled to 0° C.
3. stirringAfter stirring at 0° C. for an additional 1 hour
4. waitat ambient temperature for 3 hours
5. extractionthe mixture was extracted with EtOAc
6. washThe combined organic phases were washed with brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated
10. customThe residue was purified on a large silica gel plug
11. washeluting with hexanes