反应详情

Add 2-fluorobenzyl bromide (0.21 mL, 1.7 mmol) dropwise to a stirred suspension of (1S,2S,5R,6R)-2-(tert-butoxycarbonylamino)-4-oxo-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid (0.17 g, 0.57 mmol) and cesium carbonate (0.37 g, 1.14 mmol) in dry N,N-dimethylformamide (1.42 mL). Stir the resulting mixture at room temperature overnight under nitrogen. Quench with water and dilute with ethyl acetate. Extract the aqueous phase with ethyl acetate (3 times) and wash the organic layers with brine and water. Dry over sodium sulfate, filter and concentrate to give the crude material as a pale brown oil. Purify by flash chromatography eluting with ethyl acetate:hexane (20:80 to 30:70) to give the title compound as a pale yellow oil (229 mg, 79%). MS (m/z): 538 (M+23).

1. customQuench with water
2. additiondilute with ethyl acetate
3. extractionExtract the aqueous phase with ethyl acetate (3 times)
4. washwash the organic layers with brine and water
5. dry with materialDry over sodium sulfate
6. filtrationfilter
7. concentrationconcentrate
8. customto give the crude material as a pale brown oil
9. customPurify by flash chromatography
10. washeluting with ethyl acetate:hexane (20:80 to 30:70)