Methanesulfonyl chloride → 2-(2-Oxopyrrolidin-1-yl)ethyl methanesulfonate

HRID 1094736Notes

Reaction equation

HRID 1094736 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][CH2:6][C:5]1=[O:9].[CH3:10][S:11](Cl)(=[O:13])=[O:12]>N1C=CC=CC=1>[CH3:10][S:11]([O:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][CH2:6][C:5]1=[O:9])(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 769801-(2-Hydroxyethyl)-2-pyrrolidinone

Product 1

HCID 446271162-(2-Oxopyrrolidin-1-yl)ethyl methanesulfonateYield 72.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a Stirred solution of 1-(2-hydroxyethyl)pyrrolidin-2-one (2.6 g, 20 mmol) in pyridine (15 ml) was added methanesulfonyl chloride (2.28 g, 20 mmol) and the reaction mixture was stirred at RT overnight. Solution was concentrated and diluted with ethyl acetate (50 ml) and washed with water (50 ml). Ethyl acetate layer was separated, dried over anhydrous sodium sulfate and evaporated to yield 3.0 g of 2-(2-oxopyrrolidin-1-yl)ethyl methanesulfonate, as an oil (yield: 75%).

Workup

  1. concentrationSolution was concentrated
  2. additiondiluted with ethyl acetate (50 ml)
  3. washwashed with water (50 ml)
  4. customEthyl acetate layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-f9742ec585a441a3b7e20d03f5643e79
Source dataset
uspto-grants-2012_03
Patent number
US08133998B2

Reaction notes

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