Réaction #5210

Équation de réaction

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

Solvants

dimethylformamide

Conditions de réaction

Traitement

1. 1
   Extractionextracted with ethyl acetate
2. 2
   LavageThe extract was washed with an aqueous solution of sodium chloride
3. 3
   Séchagedried over anhydrous magnesium sulfate
4. 4
   AutreThe solvent was then removed by distillation under reduced pressure
5. 5
   Autrethe residue was purified by column chromatography through silica gel (
6. 6
   Lavageeluted with a 15:1 by volume mixture of ethyl acetate and methanol),

Mode opératoire

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.

Source