反应详情

温度

0 °C

To a solution of (S)-tert-butyl 4-((R)-2-(hydroxymethyl)pent-4-enyl)-2,2-dimethyloxazolidine-3-carboxylate (30 g, 100 mmol, 1 eq) in anhydrous THF (600 mL) was added NaH (60%, 16 g, 400 mmol, 4 eq) in portions at 0° C. The mixture was stirred for 10 min at 0° C., followed by the dropwise addition of allyl bromide (48 g, 400 mmol, 4 eq) over 15 min. After stirring for 30 min at 0° C., the mixture was allowed to warm to rt and stirred for 16 h. The reaction was quenched with aq. NH4Cl and the mixture was extracted with EA (3×). The combined organic layers were washed with brine, dried over Na2SO4, concentrated under reduced pressure to afford the crude product. It was purified by column chromatography on silica gel (PE:EA=100:1→60:1) to give (S)-tert-butyl 4-((R)-2-(allyloxymethyl)pent-4-enyl)-2,2-dimethyloxazolidine-3-carboxylate (26.15 g, 77.0%).

1. stirringAfter stirring for 30 min at 0° C.
2. temperatureto warm to rt
3. stirringstirred for 16 h
4. customThe reaction was quenched with aq. NH4Cl
5. extractionthe mixture was extracted with EA (3×)
6. washThe combined organic layers were washed with brine
7. dry with materialdried over Na2SO4
8. concentrationconcentrated under reduced pressure
9. customto afford the crude product
10. customIt was purified by column chromatography on silica gel (PE:EA=100:1→60:1)