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

HRID 553899Notes

Reaction equation

HRID 553899 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

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.

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

Sources & evidence

ORD record
ord-cf1bce33302b4751abda8045107d3748
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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