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

HRID 454319

반응식

HRID 454319 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-65b306221e8b4199ab7f562917989ec3
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492560B2

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