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

HRID 553899ノート

反応式

HRID 553899 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

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: ethyl acetate->ethyl acetate:methanol=5:1)

出典と根拠

ORDレコード
ord-cf1bce33302b4751abda8045107d3748
出典データセット
uspto-grants-2011_11
特許番号
US08048878B2

反応ノート

読み込み中…