Tetrahydrofuran → Methyl 2-(3-(benzyl oxycarbonyl)phenyl)-4-hydroxy-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

HRID 1801253Notes

Reaction equation

HRID 1801253 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](/[N:11]=[CH:12]/[C:13]2[CH:14]=[C:15]([CH:26]=[CH:27][CH:28]=2)[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])=[CH:7][CH:6]=1)=[O:4].[C:29](OCC)(=O)C.[O:35]1[CH2:39][CH2:38][CH2:37]C1>FC(F)(F)S([O-])(=O)=O.[Y+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>[CH2:19]([O:18][C:16]([C:15]1[CH:14]=[C:13]([CH:12]2[C:38]([CH3:29])([CH3:37])[CH:39]([OH:35])[C:7]3[C:8](=[CH:9][CH:10]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:6]=3)[NH:11]2)[CH:28]=[CH:27][CH:26]=1)=[O:17])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 178498127HCID 178498127, compound

Product 1

HCID 67442282Methyl 2-(3-(benzyl oxycarbonyl)phenyl)-4-hydroxy-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylateYield 78.9%

Reagents, catalysts & solvents 1

HCID 2733939Yttrium trifluoromethanesulfonateCatalyst

Procedure

To a solution of (E)-benzyl 3-((4-(methoxycarbonyl)phenylimino)methyl)benzoate (15.0 g, 40.1 mmol, 1.0 eq.), yttrium(III) trifluoromethanesulfonate (0.5 g, 0.8 mmol, 0.02 eq.) in Tetrahydrofuran (85 mL) in a four-necked flask was added Isobutyl aldehyde (3.18 g, 44.2 mmol, 1.1 eq.) via syringe. The reaction mixture was stirred at room temperature under nitrogen overnight. Thin layer chromatography (Petroleum ether:ethyl acetate=6:1) showed the reaction was complete. The reaction mixture was washed with water and the aqueous layer was extracted with ethyl acetate (twice). The organic layers were washed with brine, dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was purified by column chromatography (Petroleum ether:ethyl acetate=5:1, then 2:1) to afford 14.2 g of methyl 2-(3-(benzyl oxycarbonyl)phenyl)-4-hydroxy-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate as a yellow solid, which was used in next step without further purification. Yield: 78.9%. MS (ESI+APCI) M−17=428.1.

Workup

  1. washThe reaction mixture was washed with water
  2. extractionthe aqueous layer was extracted with ethyl acetate (twice)
  3. washThe organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by column chromatography (Petroleum ether

Sources & evidence

ORD record
ord-f34d25377ebd4e76989f259135b67a55
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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