Ethyl Acetate → HCID 24780166, compound

HRID 553918Notes

Reaction equation

HRID 553918 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:26][C@:27]1([CH3:60])[CH2:36][C@@H:35]2[N:30]([C:31](=[O:52])/[C:32](=[CH:37]/[C:38]3[CH:43]=[CH:42][C:41]([N:44]4[CH:48]=[C:47]([CH3:49])[N:46]=[CH:45]4)=[C:40]([O:50][CH3:51])[CH:39]=3)/[CH2:33][CH2:34]2)[C@H:29]([C:53]2[CH:58]=[CH:57][C:56]([F:59])=[CH:55][CH:54]=2)[CH2:28]1)(C(C)(C)C)(C)C.[Cl-].[NH4+].C(OCC)(=O)C>C1COCC1>[F:59][C:56]1[CH:57]=[CH:58][C:53]([C@@H:29]2[CH2:28][C@@:27]([OH:26])([CH3:60])[CH2:36][C@@H:35]3[N:30]2[C:31](=[O:52])/[C:32](=[CH:37]/[C:38]2[CH:43]=[CH:42][C:41]([N:44]4[CH:48]=[C:47]([CH3:49])[N:46]=[CH:45]4)=[C:40]([O:50][CH3:51])[CH:39]=2)/[CH2:33][CH2:34]3)=[CH:54][CH:55]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 69076074HCID 69076074, compound

Product 1

HCID 24780166HCID 24780166, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (1.0 M solution in THF, 404 μL) was added to a solution of (E)-(6S*,8R*,9aR*)-8-(tert-butyldimethylsilanyloxy)-6-(4-fluorophenyl)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]-8-methyloctahydroquinolizin-4-one (102 mg) in THF (2.0 mL), and the reaction solution was stirred at room temperature overnight. 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 washed with brine, dried over anhydrous 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 system->ethyl acetate-methanol system) to obtain 66.4 mg of the title compound. The property values of the compound are as follows.

Workup

  1. customthe organic layer was separated
  2. washThe resulting organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane-ethyl acetate system->ethyl acetate-methanol system)

Sources & evidence

ORD record
ord-362e0972a4634478bfe6c5a4f9e40782
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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