反应 #8271

反应方程式

sodium bicarbonate

3-(4-(1,2,5,6-tetrahydropyridyl)-3,5-difluorophenyl)-5(R)-acetoxymethyloxazolidin-2-one hydrochloride

pyridine

2,2-dimethyl-1,3-dioxolan-4(S)-ylcarbonyl chloride

→

title compound

收率 97.7%

3-(4(1-(2,2-Dimethyl-1,3-dioxolan-4(S)-ylcarbonyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)-acetoxymethyloxazolidin-2-one

收率 97.7%

溶剂

dichloromethane

dichloromethane

反应条件

后处理

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITcontinued for 30 minutes
3. 3
   其他The organic phase was separated
4. 4
   干燥dried (magnesium sulfate)
5. 5
   过滤filtered
6. 6
   其他evaporated to dryness
7. 7
   workup.ADDITIONafter the addition of toluene (20 ml)
8. 8
   其他The solid residue was triturated with a mixture of diethyl ether (250 ml) and isohexane (150 ml), and solid
9. 9
   过滤filtered

实验过程

3-(4-(1,2,5,6-tetrahydropyridyl)-3,5-difluorophenyl)-5(R)-acetoxymethyloxazolidin-2-one hydrochloride (14.5 g, 37.3 mM) was suspended in dry dichloromethane (300 ml) under nitrogen at 0°, and treated with pyridine (9.78 g, 0.12 M). A solution of 2,2-dimethyl-1,3-dioxolan-4(S)-ylcarbonyl chloride (9.59 g, 75.6 mM) in dichloromethane (100 ml) was added dropwise, and stirring continued for 3 hours, allowing the temperature to rise to ambient. Aqueous sodium bicarbonate (5%, 300 ml) was added, and stirring continued for 30 minutes. The organic phase was separated, dried (magnesium sulfate), filtered, and evaporated to dryness after the addition of toluene (20 ml). The solid residue was triturated with a mixture of diethyl ether (250 ml) and isohexane (150 ml), and solid filtered to give the title compound (17.5 g).

来源