Reacción #5200

Ecuación de reacción

sodium chloride

ethyl iodide

sodium bicarbonate

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

→

title compound

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

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente