1-(Trimethylsilyl)pyrrolidin-2-one → 3-(2-Chloropyrid 5-yl-methyl)-pyrrolid-2-one

HRID 432575

반응식

HRID 432575 반응식
C([N-]C(C)C)(C)C.[Li+].C[Si](C)(C)[N:11]1[CH2:15][CH2:14][CH2:13][C:12]1=[O:16].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26]Cl)=[CH:22][N:21]=1>C1CCCCC1.O1CCCC1>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH:13]2[CH2:14][CH2:15][NH:11][C:12]2=[O:16])=[CH:22][N:21]=1

참가 물질

6

반응물 3

HCID 844611-(Trimethylsilyl)pyrrolidin-2-oneHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 2724682Lithium diisopropylamide

생성물 1

HCID 187597883-(2-Chloropyrid 5-yl-methyl)-pyrrolid-2-one

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8078Cyclohexane용매

실험 절차

Under a nitrogen atmosphere at a temperature of from −78° C. to −60° C., 180 ml of a 1.5 molar solution of lithium diisopropylamide (IDA) in cyclohexane are added dropwise to 31.4 g of N-trimethylsilylpyrrolid-2-one in 150 ml of tetrahydrofuran (THF) and the reaction mixture is stirred at the same temperature for a further one hour. Then, at from −78° C. to −60° C., 25.5 g of 2-chloro-5-chloromethylpyridine in 40 ml of THF are added, and the mixture is stirred for a further 16 hours at that temperature and then for a further three hours at room temperature. The reaction mixture is poured onto a mixture of ice/water and extracted with ethyl acetate, and the organic phase is separated off The ethyl acetate phase is dried over sodium sulfate and concentrated to dryness by evaporation in vacuo. The residue is purified on silica gel using ethyl acetate/hexane (7:1) as eluant. The title compound having a melting point of 117-118° C. (compound 1.3) is obtained

후처리

  1. stirringthe mixture is stirred for a further 16 hours at that temperature
  2. waitfor a further three hours at room temperature
  3. extractionextracted with ethyl acetate
  4. customthe organic phase is separated off The ethyl acetate phase
  5. dry with materialis dried over sodium sulfate
  6. concentrationconcentrated to dryness by evaporation in vacuo
  7. customThe residue is purified on silica gel
  8. customis obtained

출처 및 근거

ORD 기록
ord-dec8e6cd826940d6947cf8e1fe93d861
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06664248B2

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