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

HRID 1801370Notes

Reaction equation

HRID 1801370 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 2733939Yttrium trifluoromethanesulfonateCatalyst

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-9b64cb0f78a648f2a8fb95affcf2e7b8
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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