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

HRID 2045532Notes

Reaction equation

HRID 2045532 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-8e06fde9ba774a00beaac504ef89defd
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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