Diisobutylaluminumhydride → HCID 58938660, compound

HRID 598099Notes

Reaction equation

HRID 598099 reaction equation
[CH2:1]([N:4]([CH2:30][CH2:31][CH3:32])[C:5]1[CH:6]=[C:7]([C:25](OCC)=[O:26])[C:8](=[O:24])[N:9]2[C:14]=1[CH:13]=[CH:12][CH:11]=[C:10]2[C:15]1[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=1[CH3:23])[CH2:2][CH3:3].[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1>[CH2:30]([N:4]([CH2:1][CH2:2][CH3:3])[C:5]1[CH:6]=[C:7]([CH2:25][OH:26])[C:8](=[O:24])[N:9]2[C:14]=1[CH:13]=[CH:12][CH:11]=[C:10]2[C:15]1[C:16]([CH3:23])=[CH:17][C:18]([CH3:22])=[CH:19][C:20]=1[CH3:21])[CH2:31][CH3:32]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 58938583HCID 58938583, compound

Product 1

HCID 58938660HCID 58938660, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 1-(dipropylamino)-6-mesityl-4-oxo-4H-quinolizine-3-carboxylate, (0.020 g, 0.046 mmol), in tetrahydrofuran (1 mL) was cooled to −40° C. Diisobutylaluminum hydride (1.5M, 92 mL, 0.14 mmol) was added rapidly and the solution was warmed to room temperature. The reaction was quenched with methanol and stirred with saturated Rochelle's salt for 1 h. The solution was extracted with ethyl acetate, dried over sodium sulfate, filtered and concentrated. Flash chromatography (25% ethyl acetate/hexanes) gave 0.0107 g (59% yield) of the title compound as a yellow solid.

Workup

  1. customThe reaction was quenched with methanol
  2. extractionThe solution was extracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-75f19786b50c409aaf0e38f871a296f5
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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