Cesium carbonate → 1-[2-(4-Hydroxymethyl-phenyl)-ethyl]-4-phenethyl-1H-pyridin-2-one

HRID 564158

Reaktionsgleichung

Reaktionsgleichung von HRID 564158
[CH2:1]([C:9]1[CH:14]=[CH:13][NH:12][C:11](=[O:15])[CH:10]=1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][OH:32])=[CH:27][CH:26]=1>CN(C=O)C.CCOC(C)=O.O.CO>[OH:32][CH2:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][CH2:23][N:12]2[CH:13]=[CH:14][C:9]([CH2:1][CH2:2][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)=[CH:10][C:11]2=[O:15])=[CH:26][CH:27]=1

Komponenten

8

Edukt 3

HCID 10796Cesium carbonateHCID 2680294-(2-Phenylethyl)pyridin-2(1h)-oneHCID 18402547[4-(2-Iodo-ethyl)-phenyl]-methanol

Produkt 1

HCID 670073171-[2-(4-Hydroxymethyl-phenyl)-ethyl]-4-phenethyl-1H-pyridin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 887MethanolKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To 200 mg (1.01 mmol) 4-phenethyl-1H-pyridin-2-one in 1.0 mL DMF is added at 0° C. 650 mg (2.01 mmol) cesium carbonate and the mixture is stirred 15 min at 0° C. Then 0.53 g (2.01 mmol) [4-(2-iodo-ethyl)-phenyl]-methanol (preparation 1b) is added, the mixture is warmed to RT and is stirred overnight at RT. The reaction mixture is diluted with EtOAc, water and a few drops of MeOH, the layers are separated and the organic phase is washed with water, dried over MgSO4, filtered and the solvent is evaporated. The residue is dissolved in MeOH/DMF and is purified via HPLC chromatography (Zorbax stable bond, C18; water (0.15% formic acid)/acetonitrile 95:5 to 10:90).

Aufarbeitung

  1. customthe layers are separated
  2. washthe organic phase is washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent is evaporated
  6. dissolutionThe residue is dissolved in MeOH/DMF
  7. customis purified via HPLC chromatography (Zorbax stable bond, C18; water (0.15% formic acid)/acetonitrile 95:5 to 10:90)

Quellen und Nachweise

ORD-Eintrag
ord-d8192c0675c34e4f95759f7bff0b4e78
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067590B2

Verknüpfte Notizen

Wird geladen…