4-Toluenesulfonyl chloride → (5R)-5-(p-toluenesulphonylmethyl)-2-pyrrolidinone

HRID 1791838Notes

Reaction equation

HRID 1791838 reaction equation
O[CH2:2][C@@H:3]1[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1.[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15]([CH2:2][C@@H:3]2[NH:7][C:6](=[O:8])[CH2:5][CH2:4]2)(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 7128291(R)-(-)-5-(Hydroxymethyl)-2-pyrrolidinone

Product 1

HCID 57059127(5R)-5-(p-toluenesulphonylmethyl)-2-pyrrolidinoneYield 94.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (5R)-5-hydroxymethyl-2-pyrrolidinone (5.0 g, 43 mmol) in methylene chloride (100 ml) was added 4-dimethylaminopyridine (15.7 g, 129 mmol) and p-toluenesulphonyl chloride (9.0 g, 47 mmol). The reaction was stirred at ambient temperature for 16 hours. The reaction was then washed with 1M hydrochloric acid and the organic layer separated. This was then dried over MgSO4, filtered and evaporated to give (5R)-5-(p-toluenesulphonylmethyl)-2-pyrrolidinone (10.3 g, 89%) as a white solid.

Workup

  1. washThe reaction was then washed with 1M hydrochloric acid
  2. customthe organic layer separated
  3. dry with materialThis was then dried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-f5c5f32b27054ef198d09aaf03cb0ca3
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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