Sodium Hydroxide → 1-Benzylpyrrolidin-3-yl methanesulfonate

HRID 983652Notes

Reaction equation

HRID 983652 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:14][S:15](Cl)(=[O:17])=[O:16].[OH-].[Na+]>C1(C)C=CC=CC=1.O>[CH3:14][S:15]([O:13][CH:10]1[CH2:11][CH2:12][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9]1)(=[O:17])=[O:16]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 69889N-benzyl-3-pyrrolidinol

Product 1

HCID 98998111-Benzylpyrrolidin-3-yl methanesulfonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

Thus, for example, when 1-benzyl-3-pyrrolidinol is reacted with methanesulfonyl chloride in the presence of sodium hydroxide using a mixed solvent composed of toluene and water as the reaction solvent and the reaction mixture is obtained in the form of a two-phase system composed of a toluene phase and an aqueous phase, it is possible to obtain 1-benzyl-3-pyrrolidinol methanesulfonate as a concentrate by removing the solvent by concentrating, under reduced pressure, from the toluene solution obtained by phase separation of the reaction mixture, after or without washing the toluene phase with water.

Workup

  1. customthe reaction mixture is obtained in the form of a two-phase system

Sources & evidence

ORD record
ord-09571173f85d4dca9c5ff098f25f5fe6
Source dataset
uspto-grants-2005_03
Patent number
US06864372B2

Reaction notes

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