Ethyl 5-[4-(9H-9-Carbazolyl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydro-2-quinolinyl]pentanoate → 5-[4-(9H-9-Carbazolyl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydro-2-quinolinyl]pentanoic acid

HRID 585385

Reaktionsgleichung

Reaktionsgleichung von HRID 585385
[CH:1]1[C:13]2[N:12]([CH:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]([C:24](=[O:35])[C:25]4[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=4)[CH:16]([CH2:36][CH2:37][CH2:38][CH2:39][C:40]([O:42]CC)=[O:41])[CH2:15]3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1>O1CCCC1.[OH-].[Na+].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH:1]1[C:13]2[N:12]([CH:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]([C:24](=[O:35])[C:25]4[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=4)[CH:16]([CH2:36][CH2:37][CH2:38][CH2:39][C:40]([OH:42])=[O:41])[CH2:15]3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 1

HCID 22339243Ethyl 5-[4-(9H-9-Carbazolyl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydro-2-quinolinyl]pentanoate

Produkt 1

HCID 223392535-[4-(9H-9-Carbazolyl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydro-2-quinolinyl]pentanoic acidAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

Ethyl 5-[4-(9H-9-carbazolyl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydro-2-quinolinyl]pentanoate (0.20 g, 0.34 mmol) prepared in Example 127 was dissolved in tetrahydrofuran (10 ml), to which 1N NaOH (5 ml) and tetrabutylammonium bromide (0.11 g, 0.34 mmol) were then added and stirred at room temperature for 4 hours and then at 60° C. for 4 hours. After the reaction mixture was partitioned between ethyl acetate and 1N HCl, the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was applied to silica gel column chromatography (developing solvent: ethyl acetate/hexane=1/5) to give the titled compound (0.14 g, yield: 74%) as a white crystal (cis:trans=4:1).

Aufarbeitung

  1. additionwere then added
  2. waitat 60° C. for 4 hours
  3. customAfter the reaction mixture was partitioned between ethyl acetate and 1N HCl
  4. washthe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationAfter distilling off the solvent

Quellen und Nachweise

ORD-Eintrag
ord-9eca8aaea73f4da58b6a33d96b03e621
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06930104B2

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