Reaction #5210

Reaction equation

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

Solvents

dimethylformamide

Conditions

Workup

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

Procedure

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