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

HRID 454319

Reaction equation

HRID 454319 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-65b306221e8b4199ab7f562917989ec3
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Linked notes

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