反応 #5202

反応方程式

formalin

sodium cyanoborohydride

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

sodium chloride

sodium hydroxide

→

title compound

収率 78.1%

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

収率 78.1%

溶媒

acetonitrile

反応条件

後処理

1. 1
   抽出extracted with ethyl acetate
2. 2
   洗浄The extract was washed with an aqueous solution of sodium chloride
3. 3
   乾燥dried over anhydrous magnesium sulfate
4. 4
   その他the solvent was removed by distillation under reduced pressure
5. 5
   その他The residue was purified by column chromatography through silica gel (eluted with ethyl acetate)

実験手順

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.

出典