反应 #1010701

反应方程式

Rochelle salt

diisobutylaluminum hydride toluene

methyl 4-{2-[({8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-yl}carbonyl)amino]-1-hydroxypropan-2-yl}benzoate

diisobutylaluminum hydride toluene

→

8-[(2,6-difluorobenzyl)oxy]-N-{1-hydroxy-2-[4-(hydroxymethyl)phenyl]propan-2-yl}-2-methylimidazo[1,2-a]pyridine-3-carboxamide

收率 60.5%

溶剂

THF

反应条件

后处理

1. 1
   workup.STIRRINGby stirring for 1 hour
2. 2
   萃取followed by extraction with ethyl acetate
3. 3
   洗涤The organic layer was washed with a saturated aqueous sodium chloride solution
4. 4
   干燥dried over anhydrous magnesium sulfate
5. 5
   其他the solvent was then evaporated
6. 6
   其他The residue was purified by silica gel column chromatography

实验过程

To a solution of 35 mg of methyl 4-{2-[({8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-yl}carbonyl)amino]-1-hydroxypropan-2-yl}benzoate in 1.4 ml of THF were added dropwise 0.17 ml of a 1 M diisobutylaluminum hydride/toluene solution at −78° C., followed by stirring at 0° C. for 3 hours. To the reaction mixture was added 0.14 ml of a 1 M diisobutylaluminum hydride/toluene solution at 0° C., followed by stirring for 1 hour. To the reaction mixture was added a saturated aqueous Rochelle salt solution, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was then evaporated. The residue was purified by silica gel column chromatography to obtain 20 mg of 8-[(2,6-difluorobenzyl)oxy]-N-{1-hydroxy-2-[4-(hydroxymethyl)phenyl]propan-2-yl}-2-methylimidazo[1,2-a]pyridine-3-carboxamide.

来源