Реакция #5202

Уравнение реакции

formalin

sodium cyanoborohydride

(2S, 4S)-2-ethylcarbamoyl-4-(4-methoxybenzylthio)-pyrrolidine

sodium chloride

sodium hydroxide

→

title compound

Выход 78.1%

(2S, 4S)-2-Ethylcarbamoyl-4-(4-methoxybenzylthio)-1-methylpyrrolidine

Выход 78.1%

Растворители

acetonitrile

Условия реакции

Обработка

1. 1
   Экстракцияextracted with ethyl acetate
2. 2
   ПромывкаThe extract was washed with an aqueous solution of sodium chloride
3. 3
   Сушкаdried over anhydrous magnesium sulfate
4. 4
   Другоеthe solvent was removed by distillation under reduced pressure
5. 5
   ДругоеThe residue was purified by column chromatography through silica gel (eluted with ethyl acetate)

Методика

3.43 ml of 35% formalin and 804 mg of sodium cyanoborohydride were added to a solution of 2.36 g of (2S, 4S)-2-ethylcarbamoyl-4-(4-methoxybenzylthio)-pyrrolidine dissolved in 42 ml of acetonitrile, and the mixture was stirred at room temperature for 40 minutes. At the end of this time, a 1N aqueous solution of sodium hydroxide was added, and the reaction mixture was poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through silica gel (eluted with ethyl acetate) to afford 1.93 g of the title compound as colorless crystals.

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