Réaction #41544

Équation de réaction

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

Solvants

ethanol

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source