Реакция #51123

Уравнение реакции

3-Chloro-4-{5-[4-(4-hydroxypentyl)bicyclo[2.2.2]oct-1-yl]-4-methyl-4H-1,2,4-triazol-3-yl}phenol

3-Chloro-4-{5-[4-(4-hydroxypentyl)bicyclo[2.2.2]oct-1-yl]-1-methyl-1-H-1,2,4-triazol-3-yl}phenol

N-methylmorpholine N-oxide

→

desired compound

5-{4-[5-(2-chloro-4-hydroxyphenyl)-4-methyl-4H-1,2,4-triazol-3-yl]bicyclo[2.2.2]oct-1-yl}pentan-2-one

Растворители

methylene chloride

Условия реакции

Обработка

1. 1
   workup.STIRRINGto stir for 2 h
2. 2
   ФильтрацияThe mixture was filtered through celite filtering agent
3. 3
   ДругоеThe product, 5-{4-[5-(2-chloro-4-hydroxyphenyl)-4-methyl4H-1,2,4-triazol-3-yl]bicyclo[2.2.2]oct-1-yl}pentan-2-one (6-L), was purified by preparative reverse phase HPLC on a C-18 silica gel column
4. 4
   workup.ADDITIONThe effluent containing the pure triazole
5. 5
   Другоеevaporated in vacuo
6. 6
   Другоеto remove most of the acetonitrile
7. 7
   Экстракцияextracted with methylene chloride
8. 8
   ЭкстракцияThe organic extract
9. 9
   Сушкаwas dried (MgSO4)
10. 10
    Другоеevaporated
11. 11
    Другоеthe residue dried under vacuum

Методика

3-Chloro-4-{5-[4-(4-hydroxypentyl)bicyclo[2.2.2]oct-1-yl]-4-methyl-4H-1,2,4-triazol-3-yl}phenol (5-K) (0.0035 g, 0.00869 mmol) was stirred in 0.5 mL of dry methylene chloride over activated 4 Å sieves. N-methylmorpholine N-oxide (0.0015 g, 0.013 mmol) was added. The mixture was allowed to stir under N2 for 15 min. Tetrapropylammonium perruthenate (0.00112 g, 0.00956 mmol) was added and the reaction was allowed to stir for 2 h. The mixture was filtered through celite filtering agent. The product, 5-{4-[5-(2-chloro-4-hydroxyphenyl)-4-methyl4H-1,2,4-triazol-3-yl]bicyclo[2.2.2]oct-1-yl}pentan-2-one (6-L), was purified by preparative reverse phase HPLC on a C-18 silica gel column using a gradient of acetonitrile-water buffered with 0.1% trifluoroacetic acid. The effluent containing the pure triazole was basified with 10% NaHCO3, evaporated in vacuo to remove most of the acetonitrile, and extracted with methylene chloride. The organic extract was dried (MgSO4) and evaporated, and the residue dried under vacuum to provide the desired compound. MS (ESI+)=402.3 (M+1).

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