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

HRID 432575ノート

反応式

HRID 432575 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8078Cyclohexane溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-dec8e6cd826940d6947cf8e1fe93d861
出典データセット
uspto-grants-2003_12
特許番号
US06664248B2

反応ノート

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