Aluminium lithium hydride → Ethyl 1-butyryl-6-mesityl-4-oxo-3,4-dihydro-2H-quinolizine-3-carboxylate

HRID 598113Notes

Reaction equation

HRID 598113 reaction equation
[C:1]([C:6]1[CH:7]=[C:8]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:9](=[O:25])[N:10]2[C:15]=1[CH:14]=[CH:13][CH:12]=[C:11]2[C:16]1[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=1[CH3:24])(=[O:5])[CH2:2][CH2:3][CH3:4].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:1]([C:6]1[CH2:7][CH:8]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:9](=[O:25])[N:10]2[C:15]=1[CH:14]=[CH:13][CH:12]=[C:11]2[C:16]1[C:17]([CH3:24])=[CH:18][C:19]([CH3:23])=[CH:20][C:21]=1[CH3:22])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58938681Ethyl 1-butyryl-6-mesityl-4-oxo-4H-quinolizine-3-carboxylate

Product 1

HCID 58938550Ethyl 1-butyryl-6-mesityl-4-oxo-3,4-dihydro-2H-quinolizine-3-carboxylateYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 1-butyryl-6-mesityl-4-oxo-4H-quinolizine-3-carboxylate (0.034 g, 0.084 mmol) was dissolved in tetrahydrofuran (1 mL). Lithium aluminum hydride (0.007 g, 0.17 mmol) was added at 0° C. After 15 minutes, the reaction was quenched with Glauber's salt. The solution was filtered, concentrated, and flash chromatographed (15% ethyl acetate/hexanes) to give the title compound (0.014 g, 41% yield).

Workup

  1. customthe reaction was quenched with Glauber's salt
  2. filtrationThe solution was filtered
  3. concentrationconcentrated
  4. customflash chromatographed (15% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-16dcd88989e74d3589d12c96a4e54e24
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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