반응 #5171

반응 방정식

sodium chloride

methyl iodide

sodium bicarbonate

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

→

title compound

수율 21.1%

(2S, 4S)-4-(4-Methoxybenzylthio)-1-methyl-2-methylcarbamoylpyrrolidine

수율 21.1%

용매

dimethylformamide

반응 조건

후처리

1. 1
   workup.WAITto stand overnight at room temperature
2. 2
   추출extracted with ethyl acetate
3. 3
   세척The extract was washed with an aqueous solution of sodium chloride
4. 4
   건조dried over anhydrous magnesium sulfate
5. 5
   기타The solvent was then removed by distillation under reduced pressure
6. 6
   기타the residue was purified by column chromatography through silica gel (
7. 7
   세척eluted with a 10:1 by volume mixture of ethyl acetate and methanol),

실험 절차

244 μl of methyl iodide and 300 mg of sodium bicarbonate were added, whilst ice-cooling, to a solution of 1.00 g of (2S, 4S)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine [prepared as described in step (4) above] dissolved in 6 ml of dry dimethylformamide. The mixture was then stirred at 0° to 5° C. for 1 hour and allowed to stand overnight at room temperature. 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 10:1 by volume mixture of ethyl acetate and methanol), to afford 222 mg of the title compound as colorless crystals, melting at 82°-84° C.

출처