تفاعل #8271

معادلة التفاعل

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

المردود 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

المردود 97.7%

المذيبات

dichloromethane

dichloromethane

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر