반응 #41544

반응 방정식

ammonium formate

1-(2-(6-benzyloxy-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

ammonium formate

→

1-(2-(6-hydroxy-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

용매

ethanol

반응 조건

후처리

1. 1
   기타the reaction liquid
2. 2
   온도was heated
3. 3
   온도under reflux for 5 hours
4. 4
   기타the reaction liquid
5. 5
   온도was further heated
6. 6
   온도under reflux for 1 hour
7. 7
   온도After cooled
8. 8
   기타the catalyst was removed through filtration through Celite
9. 9
   기타the solvent was evaporated away under reduced pressure
10. 10
    workup.ADDITIONThe resulting residue was diluted with 1 N hydrochloric acid
11. 11
    추출extracted with ethyl acetate
12. 12
    건조dried with anhydrous magnesium sulfate
13. 13
    기타The solvent was evaporated away under reduced pressure
14. 14
    기타the resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=100/0 to 99/1 to 98/2)
15. 15
    기타to obtain the entitled compound as a brown amorphous substance

실험 절차

713 mg of ammonium formate and 119 mg of 20% palladium hydroxide-carbon catalyst were added to an ethanol (20 ml) solution of 1.18 g of 1-(2-(6-benzyloxy-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone, and the reaction liquid was heated under reflux for 5 hours. 157 mg of ammonium formate and 56 mg of 20% palladium hydroxide-carbon catalyst were added to the reaction liquid, and the reaction liquid was further heated under reflux for 1 hour. After cooled, the catalyst was removed through filtration through Celite, and the solvent was evaporated away under reduced pressure. The resulting residue was diluted with 1 N hydrochloric acid, extracted with ethyl acetate, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=100/0 to 99/1 to 98/2) to obtain the entitled compound as a brown amorphous substance.

출처