Methyl fluorosulfate → (2S, 4S)-2-(N,N-Dimethylcarbamoyl)-1-ethyl-1-methyl-4-(4-methoxybenzylthio)pyrrolidinium fluorosulfonate

HRID 1030154Notes

Reaction equation

HRID 1030154 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

HCID 9870Methyl fluorosulfateHCID 57143534(2S, 4S)-2-(N,N-dimethyl-carbamoyl)-1-ethyl-4-(4-methoxybenzylthio)pyrrolidine

Product 1

HCID 86745656(2S, 4S)-2-(N,N-Dimethylcarbamoyl)-1-ethyl-1-methyl-4-(4-methoxybenzylthio)pyrrolidinium fluorosulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

128 μl of methyl fluorosulfonate were added to a solution of 438 mg of (2S, 4S)-2-(N,N-dimethyl-carbamoyl)-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.

Workup

  1. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  2. washthe residue was washed repeatedly by decantation with diethyl ether
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-a24ca79104e7445bbc8c1c664877a0b7
Source dataset
uspto-grants-1992_04
Patent number
US05104867

Reaction notes

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