反应详情

To a cooled (−78° C.) solution of (S)-4-benzyloxazolidin-2-one (10.26 g, 58 mmol, 1.0 equiv) in 100 mL THF was added dropwise n-BuLi (40 mL, 1.6 M, 64 mmol, 1.1 equiv). After stirring for 30 minutes, 4-fluorophenylacetyl chloride (10.0 g, 0.58 mmol, 1.0 equiv) was added dropwise. After stirring for an additional 30 minutes, the reaction mixture was allowed to warm to room temperature. The reaction was quenched with sat'd. aq. NH4Cl, extracted with DCM, and washed with brine. The organic layer was then dried over sodium sulfate, filtered, and concentrated in vacuo. Purification by silica gel (10-20% EtOAc/Hexanes) provided the title compound as a thick oil (14.7 g, 81%). m/z=314.3 [M+H]+.

1. stirringAfter stirring for an additional 30 minutes
2. customThe reaction was quenched with sat'd
3. extractionaq. NH4Cl, extracted with DCM
4. washwashed with brine
5. dry with materialThe organic layer was then dried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customPurification by silica gel (10-20% EtOAc/Hexanes)