反应 #92762

反应方程式

hydrochloric acid

methyl (2S,4S)-4-({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)-1-methylpyrrolidine-2-carboxylate

diisobutylaluminum hydride toluene

→

8-(cyclohexylmethoxy)-N-[(3S,5S)-5-(hydroxymethyl)-1-methylpyrrolidin-3-yl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide dihydrochloride

溶剂

dichloromethane

反应条件

后处理

1. 1
   温度cooling
2. 2
   温度cooling
3. 3
   过滤the reaction mixture was filtered over Celite
4. 4
   workup.ADDITIONto the filtrate were added ethyl acetate
5. 5
   其他a layer separation operation
6. 6
   洗涤The organic layer was washed with water and saturated brine
7. 7
   干燥dried over anhydrous magnesium sulfate
8. 8
   其他The solvent was evaporated under reduced pressure
9. 9
   其他the obtained residue was purified by silica gel column chromatography
10. 10
    其他To a solution of the obtained purified product in ethyl acetate
11. 11
    workup.ADDITIONwas added a hydrogen chloride/ethyl acetate solution
12. 12
    过滤the resulting solid was collected by filtration
13. 13
    其他dried

实验过程

To a solution of 150 mg of methyl (2S,4S)-4-({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)-1-methylpyrrolidine-2-carboxylate and 4 ml of dichloromethane was added dropwise 1.5 ml of a 1 M diisobutylaluminum hydride/toluene solution under ice-cooling, followed by stirring for 2 hours under ice-cooling. Subsequently, 1 M hydrochloric acid was added thereto, the reaction mixture was filtered over Celite, and to the filtrate were added ethyl acetate to carry out a layer separation operation. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography. To a solution of the obtained purified product in ethyl acetate was added a hydrogen chloride/ethyl acetate solution, and the resulting solid was collected by filtration and dried to obtain 25 mg of 8-(cyclohexylmethoxy)-N-[(3S,5S)-5-(hydroxymethyl)-1-methylpyrrolidin-3-yl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide dihydrochloride.

来源