Methyl fluorosulfate → (2S, 4S)-2-(N,N-Dimethylcarbamoyl)-1-ethyl-1-methyl-4-(4-methoxybenzylthio)pyrrolidinium fluorosulfonate
Reaction equation
[F:1][S:2]([O:5][CH3:6])(=[O:4])=[O:3].[CH3:7][N:8]([CH3:28])[C:9]([C@@H:11]1[CH2:15][C@H:14]([S:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[CH2:13][N:12]1[CH2:26][CH3:27])=[O:10]>C(Cl)Cl>[F:1][S:2]([O-:5])(=[O:4])=[O:3].[CH3:28][N:8]([CH3:7])[C:9]([C@@H:11]1[CH2:15][C@H:14]([S:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)[CH2:13][N+:12]1([CH2:26][CH3:27])[CH3:6])=[O:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
128 μl of methyl fluorosulfonate were added to a solution of 438 mg of (2S, 4S)-2-(N,N-dimethylcarbamoyl)-1-ethyl-4-(4-methoxybenzylthio)pyrrolidine dissolved in 10 ml of methylene chloride, and the mixture was stirred at room temperature for 2 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the residue was washed repeatedly by decantation with diethyl ether and dried under reduced pressure to afford the title compound as an oil.