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

HRID 553882Notes

Reaction equation

HRID 553882 reaction equation
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

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-7141892eb3bd4548a3f5de565832f277
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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