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

HRID 1030133Notes

Reaction equation

HRID 1030133 reaction equation
[F:1][S:2]([O:5][CH3:6])(=[O:4])=[O:3].[C:7]([C@@H:10]1[CH2:14][C@H:13]([S:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[CH2:12][N:11]1[CH3:25])(=[O:9])[NH2:8]>C(Cl)Cl>[F:1][S:2]([O-:5])(=[O:4])=[O:3].[C:7]([C@@H:10]1[CH2:14][C@H:13]([S:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)[CH2:12][N+:11]1([CH3:6])[CH3:25])(=[O:9])[NH2:8]

Participants

4

Reactant 2

HCID 9870Methyl fluorosulfateHCID 14796652(2S,4S)-2-carbamoyl-4-(4-methoxybenzylthio)-1-methylpyrrolidine

Product 1

HCID 10668350(2S, 4S)-2-Carbamoyl-4-(4-methoxybenzylthio)-1,1-dimethylpyrrolidinium fluorosulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.123 ml of methyl fluorosulfonate was added, whilst ice-cooling, to a solution of 320 mg of (2S, 4S)-2-carbamoyl-4-(4-methoxybenzylthio)-1-methylpyrrolidine [prepared as described in step (6) or (6a) above] dissolved in 7 ml of dry methylene chloride. The mixture was then stirred at the same temperature for 20 minutes and 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 repeatedly washed by decantation with diethyl ether and then dried under reduced pressure to afford 525 mg of 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 repeatedly washed by decantation with diethyl ether
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-2775f0cace794788bf595f7cbc176380
Source dataset
uspto-grants-1992_04
Patent number
US05104867

Reaction notes

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