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Ethyl Acetate → 6-(2-fluorophenyl)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]octahydroquinolizin-4-one

HRID 553914
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HRID 553914 반응식
O.[OH-].[Li+].[F:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C@@H:11]1[CH2:20][CH2:19][CH2:18][C@H:17]2[N:12]1[C:13](=[O:29])[CH:14](P(=O)(OCC)OCC)[CH2:15][CH2:16]2.[CH3:30][O:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][C:39]=1[N:40]1[CH:44]=[C:43]([CH3:45])[N:42]=[CH:41]1)[CH:35]=O.C(OCC)(=O)C>O1CCCC1.C(O)C>[F:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]1[CH2:20][CH2:19][CH2:18][CH:17]2[N:12]1[C:13](=[O:29])[C:14](=[CH:35][C:34]1[CH:37]=[CH:38][C:39]([N:40]3[CH:44]=[C:43]([CH3:45])[N:42]=[CH:41]3)=[C:32]([O:31][CH3:30])[CH:33]=1)[CH2:15][CH2:16]2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 272824453-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehydeHCID 86612702diethyl[(6S*,9aR*)-6-(2-fluorophenyl)-4-oxooctahydroquinolizin-3-yl]phosphonate

생성물 1

HCID 866325466-(2-fluorophenyl)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]octahydroquinolizin-4-one수율 83%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

실험 절차

Lithium hydroxide monohydrate (169 mg) was added to a mixed solution of diethyl [(6S*,9aR*)-6-(2-fluorophenyl)-4-oxooctahydroquinolizin-3-yl]phosphonate (501 mg) and 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (290 mg) in tetrahydrofuran (12 mL) and ethanol (4 mL) at room temperature, and the reaction solution was stirred at room temperature for two hours. Ethyl acetate was added to the reaction solution, which was then sequentially washed with saturated sodium bicarbonate water and brine. The resulting organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane-ethyl acetate system) to obtain 483 mg of the title compound. The property values of the compound are as follows.

후처리

  1. washwas then sequentially washed with saturated sodium bicarbonate water and brine
  2. dry with materialThe resulting organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane-ethyl acetate system)

출처 및 근거

ORD 기록
ord-4c7a53c4b7ed4088b8627a656bad94d6
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08048878B2

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