反应详情

A solution of 5-(5-trifluoromethyl-pyridin-2-yloxy)-pyridin-2-ol (180 mg, 0.70 mmol), 3-[4-(tert-butyl-dimethyl-silanyloxy)-piperidine-1-carbonyl]-1-methyl-3H-imidazol-1-ium iodide (317 mg, 0.70 mmol) and triethylamine (98 μL) in acetonitrile (10 mL) was stirred at room temperature overnight. The solvent was evaporated in vacuo. The residue was redissolved in some dichloromethane, chloromethane, filtered over a short pad of silicagel and washed with ethyl acetate:heptane 50:50. The solvent was evaporated in vacuo and the residue was dissolved in 3.2N HCl in ether (10 mL). After stirring for 1 hour at room temperature the solvent was evaporated in vacuo and the residue was dissolved in dichloromethane. Triethylamine (0.5 mL) was added and the solution was extracted with water. The organic layer was dried over sodium sulphate, filtered and evaporated in vacuo to yield the title compound (174 mg, 65% yield) as a thick oil.

1. customThe solvent was evaporated in vacuo
2. dissolutionThe residue was redissolved in some dichloromethane, chloromethane
3. filtrationfiltered over a short pad of silicagel
4. washwashed with ethyl acetate:heptane 50:50
5. customThe solvent was evaporated in vacuo
6. dissolutionthe residue was dissolved in 3.2N HCl in ether (10 mL)
7. customwas evaporated in vacuo
8. dissolutionthe residue was dissolved in dichloromethane
9. additionTriethylamine (0.5 mL) was added
10. extractionthe solution was extracted with water
11. dry with materialThe organic layer was dried over sodium sulphate
12. filtrationfiltered
13. customevaporated in vacuo