1-(Bromomethyl)-4-(trifluoromethyl)benzene → 3-[4-(Trifluoromethyl)benzyl]pyrrolidin-2-one

HRID 2235300ノート

反応式

HRID 2235300 の反応式
C([Si](C)(C)O[C@@H]1CC[C@H]([N:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])CC1)(C)(C)C.[F:21][C:22]([F:32])([F:31])[C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Br)=[CH:25][CH:24]=1.[Li+].CC([N-]C(C)C)C>>[F:21][C:22]([F:31])([F:32])[C:23]1[CH:30]=[CH:29][C:26]([CH2:27][CH:15]2[CH2:16][CH2:17][NH:13][C:14]2=[O:18])=[CH:25][CH:24]=1

参加物

4

反応物 3

HCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 2724682Lithium diisopropylamideHCID 178455336HCID 178455336、化合物

生成物 1

HCID 713002843-[4-(Trifluoromethyl)benzyl]pyrrolidin-2-one収率 39%

実験手順

Using the procedure to synthesize Example 202 and using cis-1-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-pyrrolidin-2-one (Preparation 17), 4-trifluoromethyl benzylbromide and 1.5 equivalents of LDA affords an oil. Chromatography (silica, 4:1 hexanes/EtoAc) yields 4-[4-tert-butyl dimethyl-silanyloxy)-cyclohexyl]-3-(4-trifluoromethyl-benzyl)-pyrrolidin-2-one in 39% yield. The silylether is dissolved in THF, treated with 5.0 equivalents of TBAF and allowed to stir at room temperature overnight. Quench reaction with water, dilute with methylene chloride, separate, dry over sodium sulfate, filter and evaporate. Chromatography (silica, 4:6 hexanes/EtoAc) provides the titled compound in 21% yield: Mass spectrum (API-ES positive) m/z=342.3 (M+H).

後処理

  1. customto synthesize Example 202
  2. customaffords an oil

出典と根拠

ORDレコード
ord-abcfaccec3c94a8f81f5508888172a81
出典データセット
uspto-grants-2010_05
特許番号
US07713979B2

反応ノート

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