Methyl fluorosulfate → (3S)-1,1-Dimethyl-3-(4-methoxybenzylthio)pyrrolidinium fluorosulfonate

HRID 5090

Reaction equation

HRID 5090 reaction equation
[F:1][S:2]([O:5][CH3:6])(=[O:4])=[O:3].[CH3:7][O:8][C:9]1[CH:22]=[CH:21][C:12]([CH2:13][S:14][C@H:15]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16]2)=[CH:11][CH:10]=1>C(Cl)Cl>[F:1][S:2]([O-:5])(=[O:4])=[O:3].[CH3:20][N+:17]1([CH3:6])[CH2:18][CH2:19][C@H:15]([S:14][CH2:13][C:12]2[CH:11]=[CH:10][C:9]([O:8][CH3:7])=[CH:22][CH:21]=2)[CH2:16]1

Participants

4

Reactant 2

HCID 9870Methyl fluorosulfateHCID 57243155HCID 57243155, compound

Product 1

HCID 10784133(3S)-1,1-Dimethyl-3-(4-methoxybenzylthio)pyrrolidinium fluorosulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

118 μl of methyl fluorosulfonate were added, whilst ice-cooling, to a solution of 340 mg of (3S)-3-(4-methoxybenzylthio)-1-methylpyrrolidine [prepared as described in step (4) above] dissolved in 20 ml of dry methylene chloride. The mixture was then stirred at the same temperature for 30 minutes and then at room temperature for 3.5 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 dried under reduced pressure to afford 500 mg of the title compound as a colorless powder.

Workup

  1. waitat room temperature for 3.5 hours
  2. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  3. washthe residue was repeatedly washed by decantation with diethyl ether
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-3f825583ac204effbee8944eb1dc37d3
Source dataset
uspto-grants-1993_09
Patent number
US05242914

Linked notes

Loading…