Ethyl Acetate → (E)-(6S*,9aR*)-6-(4-hydroxymethylphenyl)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]octahydroquinolizin-4-one

HRID 553899노트

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HRID 553899 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:34]=[CH:35][C:36]=1[N:37]1[CH:41]=[C:40]([CH3:42])[N:39]=[CH:38]1)/[CH:12]=[C:13]1/[C:14](=[O:33])[N:15]2[C@@H:20]([CH2:21][CH2:22]/1)[CH2:19][CH2:18][CH2:17][C@H:16]2[C:23]1[CH:32]=[CH:31][C:26]([C:27](OC)=[O:28])=[CH:25][CH:24]=1.[Cl-].[NH4+].C(OCC)(=O)C>C1COCC1>[OH:28][CH2:27][C:26]1[CH:31]=[CH:32][C:23]([C@@H:16]2[CH2:17][CH2:18][CH2:19][C@H:20]3[N:15]2[C:14](=[O:33])/[C:13](=[CH:12]/[C:11]2[CH:34]=[CH:35][C:36]([N:37]4[CH:41]=[C:40]([CH3:42])[N:39]=[CH:38]4)=[C:9]([O:8][CH3:7])[CH:10]=2)/[CH2:22][CH2:21]3)=[CH:24][CH:25]=1

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 24779885methyl (E)-4-{(4S*,9aR*)-7-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]-6-oxooctahydroquinolizin-4-yl}benzoate

생성물 1

HCID 24779886(E)-(6S*,9aR*)-6-(4-hydroxymethylphenyl)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]octahydroquinolizin-4-one수율 50.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

Lithium aluminum hydride (4 mg) was added to a solution of methyl (E)-4-{(4S*,9aR*)-7-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]-6-oxooctahydroquinolizin-4-yl}benzoate (50 mg) in THF (1 mL) at 0° C., and the reaction solution was stirred at 0° C. for two hours. A saturated ammonium chloride solution and ethyl acetate were added to the reaction solution, and the organic layer was separated. 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: ethyl acetate->ethyl acetate:methanol=5:1) to obtain 24 mg of the title compound. The property values of the compound are as follows.

후처리

  1. customthe organic layer was separated
  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: ethyl acetate->ethyl acetate:methanol=5:1)

출처 및 근거

ORD 기록
ord-cf1bce33302b4751abda8045107d3748
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08048878B2

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