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

HRID 2235300Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2235300
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

Komponenten

4

Edukt 3

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

Produkt 1

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

Versuchsvorschrift

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).

Aufarbeitung

  1. customto synthesize Example 202
  2. customaffords an oil

Quellen und Nachweise

ORD-Eintrag
ord-abcfaccec3c94a8f81f5508888172a81
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07713979B2

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