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

HRID 2235300노트

반응식

HRID 2235300 반응식
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

참가 물질

4

반응물 3

HCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 2724682Lithium diisopropylamideHCID 178455336HCID 178455336, 화합물

생성물 1

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

실험 절차

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).

후처리

  1. customto synthesize Example 202
  2. customaffords an oil

출처 및 근거

ORD 기록
ord-abcfaccec3c94a8f81f5508888172a81
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07713979B2

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