Реакция #5212

Уравнение реакции

sodium hydride

(2S, 4S)-1-(2-methanesulfonyloxyethyl)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine

sodium chloride

→

title compound

Выход 87.1%

(6S, 8S)-8-(4-Methoxybenzylthio)-4-methyl-5-oxo-1,4-diazabicyclo[4.3.0]nonane

Выход 87.1%

Растворители

dimethylformamide

Условия реакции

Обработка

1. 1
   workup.WAITat 30° C. for 2 hours
2. 2
   Экстракцияextracted with ethyl acetate
3. 3
   ПромывкаThe extract was washed with an aqueous solution of sodium chloride
4. 4
   Сушкаdried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONfreed from the solvent by distillation under reduced pressure
6. 6
   ДругоеThe residue was purified by column chromatography through silica gel (
7. 7
   Промывкаeluted with a 5:1 by volume mixture of acetonitrile and methanol),

Методика

347 mg of sodium hydride (as a 55% w/w suspension in mineral oil) was added, whilst ice-cooling, to a solution of 2.64 g of (2S, 4S)-1-(2-methanesulfonyloxyethyl)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine dissolved in 30 ml of dry dimethylformamide, and the mixture was stirred at 0° to 5° C. for 30 minutes and then at 30° C. for 2 hours. The reaction mixture was then poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and freed from the solvent by distillation under reduced pressure. The residue was purified by column chromatography through silica gel (eluted with a 5:1 by volume mixture of acetonitrile and methanol), to afford 1.75 g of the title compound as an oil.

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