Ethanol → ethyl 1-cyclopropyl-9-methyl-8-(1-methylisoindoline-5-yl)-4-oxo-4H-quinolizine-3-carboxylate

HRID 1061437Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1061437
Cl[C:2]1[CH:3]=[CH:4][N:5]2[C:10]([C:11]=1[CH3:12])=[C:9]([CH:13]1[CH2:15][CH2:14]1)[CH:8]=[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:6]2=[O:21].[CH2:22](O)[CH3:23].[C:25](=O)([O-])[O-].[Na+].[Na+].C[C:32]1[C:37]([CH3:38])=[CH:36][CH:35]=[CH:34][N:33]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH:13]1([C:9]2[CH:8]=[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:6](=[O:21])[N:5]3[C:10]=2[C:11]([CH3:12])=[C:2]([C:25]2[CH:38]=[C:37]4[C:36](=[CH:35][CH:34]=2)[CH:22]([CH3:23])[NH:33][CH2:32]4)[CH:3]=[CH:4]3)[CH2:15][CH2:14]1

Komponenten

7

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 114202,3-LutidineHCID 12071709ethyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate

Produkt 1

HCID 18629334ethyl 1-cyclopropyl-9-methyl-8-(1-methylisoindoline-5-yl)-4-oxo-4H-quinolizine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

226.8 mg of ethyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (XIII) was suspended in 3 ml of toluene, and 1.6 ml of ethanol, 0.82 ml of a 2M sodium carbonate solution, 311.1 mg of (+)-1-methyl-2-tritylisoindoline-5-boric acid (3) and 23.2 mg of bis(triphenylphosphin)paradium (II) chloride were added thereto, and thereafter, under an argon atmosphere, the resulting mixture was heated under reflux for 4 hours. Ethyl acetate was added to the reaction solution and the organic layer was separated and rinsed with water, and thereafter, dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:1) to obtain 335.9 mg of ethyl 1-cyclopropyl-9-methyl-8-(1-methylisoindoline-5-yl)-4-oxo-4H-quinolizine-3-carboxylate (XIV).

Aufarbeitung

  1. temperatureunder an argon atmosphere, the resulting mixture was heated
  2. temperatureunder reflux for 4 hours
  3. customthe organic layer was separated
  4. washrinsed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-6251aa7ed37b48e9ac694adbe7c95a96
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06525066B2

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