Methyl fluorosulfate → (2S, 4S)-2-(N,N-Dimethylcarbamoyl)-4-(4-methoxybenzylthio)-1,1-dimethylpyrrolidinium fluorosulfonate

HRID 5086

Reaction equation

HRID 5086 reaction equation
[F:1][S:2]([O:5][CH3:6])(=[O:4])=[O:3].[CH3:7][N:8]([CH3:27])[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[CH3:26])=[O:10]>C(Cl)Cl>[F:1][S:2]([O-:5])(=[O:4])=[O:3].[CH3:7][N:8]([CH3:27])[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([CH3:6])[CH3:26])=[O:10]

Participants

4

Reactant 2

HCID 9870Methyl fluorosulfateHCID 57114883(2S, 4S)-2-(N,N-Dimethylcarbamoyl)-4-(4-methoxybenzylthio)-1-methylpyrrolidine

Product 1

HCID 86747189(2S, 4S)-2-(N,N-Dimethylcarbamoyl)-4-(4-methoxybenzylthio)-1,1-dimethylpyrrolidinium fluorosulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

139 μl of methyl fluorosulfonate were added, whilst ice-cooling, to a solution of 190 mg of (2S, 4S)-2-(N,N-dimethylcarbamoyl)-4-(4-methoxybenzylthio)-1-methylpyrrolidine [prepared as described in step (5) or (11) above] dissolved in 3.8 ml of methylene chloride, and the mixture was stirred at room temperature for 2 hours. At the end of this time, the solvent was distilled off under reduced pressure. The residue was repeatedly washed by decantation with hexane and dried under reduced pressure, to give 356 mg of the title compound as an oil.

Workup

  1. distillationAt the end of this time, the solvent was distilled off under reduced pressure
  2. washThe residue was repeatedly washed by decantation with hexane
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-57c4dcadfa504bd3b6a8c19ef17eb2ac
Source dataset
uspto-grants-1993_09
Patent number
US05242914

Linked notes

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