Réaction #5176

Équation de réaction

sodium bicarbonate

sodium bicarbonate

methyl iodide

(2S, 4S)-2-(N,N-dimethylcarbamoyl)-4-(4-methoxybenzylthio)pyrrolidine

→

title compound

Rendement 26.4%

(2S, 4S)-2-(N,N-Dimethylcarbamoyl)-4-(4-methoxybenzylthio)-1-methylpyrrolidine

Rendement 26.4%

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 chromatography

Mode opératoire

84 mg of sodium bicarbonate and 41 μl of methyl iodide were added, whilst ice-cooling, to a solution of 163 mg of (2S, 4S)-2-(N,N-dimethylcarbamoyl)-4-(4-methoxybenzylthio)pyrrolidine [prepared as described in step (4) above] dissolved in 1.5 ml of dry dimethylformamide, and the mixture was stirred at room temperature for 4 hours. At the end of this time, the reaction mixture was poured into a saturated aqueous solution of sodium bicarbonate 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 chromatography using a Lobar column (Merck, LiChroprep Si60, size A). 45 mg of the title compound were obtained, as an oil, from the fractions eluted with a 3:1 by volume mixture of ethyl acetate and methanol.

Source