反应详情

To a solution of (+/−)-4-(5-methylcyclohexa-1,3-dienyl)-3-nitropyridine (1.0 equiv.) in DCM (0.1M) at 0° C. was added m-CPBA (1.1 equiv.) and the reaction was allowed to warm to room temperature. After 3 hours, the mixture was quenched with saturated NaHCO3, extracted with DCM, and the organic phase was dried with sodium sulfate, filtered, and concentrated to give a yellow oil. The crude was dissolved in ethanol and water (3:1, 0.1 M), and sodium azide (2.0 equiv.) and ammonium chloride (2.0 equiv.) were added. The reaction was stirred for 4 hours, then concentrated in vacuo. To the crude was added ethyl acetate and water, the organic phase was washed with brine, dried with sodium sulfate, filtered, and concentrated. The crude material was purified via silica gel column chromatography eluting with ethyl acetate and hexanes (1:1) to afford (+/−)-2-azido-6-methyl-4-(3-nitropyridin-4-yl)cyclohex-3-enol as an oil in 49% yield. LC/MS=276.1 (M+H), Rt=0.71 min.

1. customthe mixture was quenched with saturated NaHCO3
2. extractionextracted with DCM
3. dry with materialthe organic phase was dried with sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated
6. customto give a yellow oil
7. concentrationconcentrated in vacuo
8. additionTo the crude was added ethyl acetate and water
9. washthe organic phase was washed with brine
10. dry with materialdried with sodium sulfate
11. filtrationfiltered
12. concentrationconcentrated
13. customThe crude material was purified via silica gel column chromatography
14. washeluting with ethyl acetate and hexanes (1:1)