反应详情

Add 4-fluorobenzamidoxime (4.61 g, 29.93 mmol) to a 1M solution of potassium t-butoxide (27.6 mL, 27.63 mmol) in tetrahydrofuran. Add methyl 3-tert-butyl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-7-carboxylate (6.07 g, 23.02 mmol) and stir overnight at room temperature. Dissolve the reaction in a 1:1 mixture of 50% saturated aqueous sodium bicarbonate and ethyl acetate. Separate layers and extract the aqueous layer with additional ethyl acetate. Wash the combined organic layers with brine, dry over anhydrous sodium sulfate, filter, and concentrate under reduced pressure. Purify the resulting residue by flash chromatography (silica gel), eluting with first 25-100% ethyl acetate:hexane and then 5% methanol in ethyl acetate. Recrystallize from dichloromethane and hexane to afford the title compound as a white solid (3.96 g). Mass spectrum (m/z): 342 (M+1).

1. dissolutionDissolve
2. customthe reaction
3. extractionSeparate layers and extract the aqueous layer with additional ethyl acetate
4. washWash the combined organic layers with brine
5. dry with materialdry over anhydrous sodium sulfate
6. filtrationfilter
7. concentrationconcentrate under reduced pressure
8. customPurify the resulting residue by flash chromatography (silica gel)
9. washeluting with first 25-100% ethyl acetate
10. customRecrystallize from dichloromethane and hexane