Reaction #5200

Reaction equation

sodium chloride

ethyl iodide

sodium bicarbonate

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

→

title compound

(2S, 4S)-1-Ethyl-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine

Solvents

dimethylformamide

Conditions

Workup

1. 1
   workup.WAITat room temperature for 5 hours
2. 2
   Extractionextracted with ethyl acetate
3. 3
   WashThe extract was washed with an aqueous solution of sodium chloride
4. 4
   Dryingdried over anhydrous magnesium sulfate
5. 5
   Otherafter which the solvent was removed by distillation under reduced pressure
6. 6
   OtherThe residue was purified by column chromatography (eluted with ethyl acetate)

Procedure

0.71 ml of ethyl iodide and 742 mg of sodium bicarbonate were added to a solution of 2.25 g of (2S, 4S)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine dissolved in 20 ml of dry dimethylformamide, and the mixture was stirred at 0° to 5° C. for 1 hour and then at room temperature for 5 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, after which the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (eluted with ethyl acetate), to afford 1.87 g of the title compound as colorless crystals, melting at 68°-70° C.

Source