Tetrahydrofuran → Methyl 2-(3-(benzyloxycarbonyl)phenyl)-4-hydroxy-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-8-carboxylate

HRID 2045650Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2045650
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH:12]([C:14]1[CH:15]=[C:16]([CH:27]=[CH:28][CH:29]=1)[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])=O.[C:30](OCC)(=O)C.[O:36]1[CH2:40][CH2:39][CH2:38]C1>FC(F)(F)S([O-])(=O)=O.[Y+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>[CH2:20]([O:19][C:17]([C:16]1[CH:15]=[C:14]([CH:12]2[C:39]([CH3:30])([CH3:38])[CH:40]([OH:36])[C:11]3[C:2](=[C:3]([C:4]([O:6][CH3:7])=[O:5])[CH:8]=[CH:9][CH:10]=3)[NH:1]2)[CH:29]=[CH:28][CH:27]=1)=[O:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 8635Methyl AnthranilateHCID 8857Ethyl AcetateHCID 23286083Benzyl 3-formylbenzoate

Produkt 1

HCID 67443442Methyl 2-(3-(benzyloxycarbonyl)phenyl)-4-hydroxy-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-8-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2733939Yttrium trifluoromethanesulfonateKatalysator

Versuchsvorschrift

To a mixture of methyl 2-aminobenzoate (0.77 g, 5.1 mmol) and benzyl 3-formylbenzoate (1.23 g, 5.1 mmol) in tetrahydrofuran (20.5 mL) was added isobutyl aldehyde (0.48 g, 6.68 mmol), followed by yttrium(III) trifluoromethanesulfonate (159 mg, 0.26 mmol), the reaction mixture was stirred at room temperature under nitrogen atmosphere for 23 h, Thin layer chromatography (petroleum ether:ethyl acetate=10:1) showed the reaction was nearly complete. The reaction was quenched by brine and separated. The aqueous layer was extracted with Ethyl acetate (twice) and the combined organic layers were washed with brine, dried over anhydrous magnesium sulfate. Removal of the solvent in vacuo and the residue was purified by column chromatography (petroleum ether:ethyl acetate=20:1) to afford 0.66 g of methyl 2-(3-(benzyloxycarbonyl)phenyl)-4-hydroxy-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-8-carboxylate as a yellow oil, which was used in next step without further purification.

Aufarbeitung

  1. customThe reaction was quenched by brine
  2. customseparated
  3. extractionThe aqueous layer was extracted with Ethyl acetate (twice) and the combined organic layers
  4. washwere washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customRemoval of the solvent in vacuo
  7. customthe residue was purified by column chromatography (petroleum ether:ethyl acetate=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-401f01c51fa346c6b6065a2dde5476b0
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586747B2

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