反応 #5210

反応方程式

sodium chloride

2-iodoethanol

sodium bicarbonate

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

→

title compound

(2S, 4S)-1-(2-hydroxyethyl)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidin

溶媒

dimethylformamide

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 then removed by distillation under reduced pressure
5. 5
   その他the residue was purified by column chromatography through silica gel (
6. 6
   洗浄eluted with a 15:1 by volume mixture of ethyl acetate and methanol),

実験手順

934 μl of 2-iodoethanol and 1.01 g of sodium bicarbonate were added, whilst ice-cooling, to a solution of 2.80 g of (2S, 4S)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine dissolved in 18 ml of dry dimethylformamide, and the mixture was stirred at 40° C. for 24 hours. At the end of this time, 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. The solvent was then removed by distillation under reduced pressure, and the residue was purified by column chromatography through silica gel (eluted with a 15:1 by volume mixture of ethyl acetate and methanol), to afford 2.22 g of the title compound as colorless crystals, melting at 88°-89.5° C.

出典