反応 #41544

反応方程式

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

溶媒

ethanol

反応条件

後処理

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

実験手順

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.

出典