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

HRID 553882
ノート
印刷プレビュー

反応式

HRID 553882 の反応式
O.[OH-].[Li+].[CH3:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C@@H:12]2[CH2:21][CH2:20][CH2:19][C@H:18]3[N:13]2[C:14](=[O:30])[CH:15](P(=O)(OCC)OCC)[CH2:16][CH2:17]3)=[CH:8][CH:7]=1.[CH3:31][O:32][C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][C:40]=1[N:41]1[CH:45]=[C:44]([CH3:46])[N:43]=[CH:42]1)[CH:36]=O.C(OCC)(=O)C>O1CCCC1.C(O)C.[Cl-].[Na+].O>[CH3:31][O:32][C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][C:40]=1[N:41]1[CH:45]=[C:44]([CH3:46])[N:43]=[CH:42]1)/[CH:36]=[C:15]1\[CH2:16][CH2:17][C@H:18]2[N:13]([C:14]\1=[O:30])[C@@H:12]([C:9]1[CH:8]=[CH:7][C:6]([O:5][CH3:4])=[CH:11][CH:10]=1)[CH2:21][CH2:20][CH2:19]2
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 272824453-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehydeHCID 86612697diethyl [(6S*,9aR*)-6-(4-methoxyphenyl)-4-oxooctahydroquinolizin-3-yl]phosphonate

生成物 1

HCID 24782063(E)-(6R*,9aS*)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]-6-(4-methoxyphenyl)octahydroquinolizin-4-one
収率 69.6%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

Lithium hydroxide monohydrate (11 mg) was added to a mixed solution of diethyl [(6S*,9aR*)-6-(4-methoxyphenyl)-4-oxooctahydroquinolizin-3-yl]phosphonate (35 mg) and 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (19 mg) in tetrahydrofuran (2 mL) and ethanol (0.5 mL), and the reaction solution was stirred at room temperature for three hours. Ethyl acetate and brine 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: heptane:ethyl acetate=1:1->ethyl acetate) to obtain 28 mg of the title compound. The property values of the compound are as follows.

後処理

  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: heptane:ethyl acetate=1:1->ethyl acetate)

出典と根拠

ORDレコード
ord-7141892eb3bd4548a3f5de565832f277
出典データセット
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08048878B2

反応ノート

読み込み中…

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