Reaktion #41544

Reaktionsgleichung

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

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle