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

HRID 564158

반응식

HRID 564158 반응식
[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

참가 물질

8

반응물 3

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

생성물 1

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

시약·촉매·용매 4

HCID 887Methanol촉매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-d8192c0675c34e4f95759f7bff0b4e78
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067590B2

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