HCID 178498129, compound → HCID 67442141, compound

HRID 2045675Notes

Reaction equation

HRID 2045675 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C:4]([CH3:25])([O:6][C:7]1[CH:8]=[C:9]([CH:22]=[CH:23][CH:24]=1)/[CH:10]=[N:11]/[C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=1)[CH3:5]>O1CCCC1.FC(F)(F)S([O-])(=O)=O.[Y+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>[OH:2][CH:3]1[C:21]2[C:12](=[CH:13][CH:14]=[C:15]([C:16]([O:18][CH3:19])=[O:17])[CH:20]=2)[NH:11][CH:10]([C:9]2[CH:22]=[CH:23][CH:24]=[C:7]([O:6][C:4]([CH3:5])([CH3:25])[C:3]([O:2][CH3:1])=[O:26])[CH:8]=2)[C:4]1([CH3:25])[CH3:5]

Participants

4

Reactant 1

HCID 178498129HCID 178498129, compound

Product 1

HCID 67442141HCID 67442141, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 2733939Yttrium trifluoromethanesulfonateCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (E)-methyl 4-(3-(1-methoxy-2-methyl-1-oxopropan-2-yloxy)benzylideneamino)benzoate (888 mg, 2.5 mmol) and yttrium(III) trifluoromethanesulfonate (5 mL) in tetrahydrofuran (6 mL) was added a solution of isobutyl aldehyde (216 mg, 3.0 mmol) in tetrahydrofuran (1 mL) under nitrogen. The mixture was stirred at room temperature for 17 h. The mixture was purified by column chromatography to afford 510 mg of methyl 4-hydroxy-2-(3-(1-methoxy-2-methyl-1-oxopropan-2-yloxy)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate as a white solid. (Yield: 48%, 2 steps).

Workup

  1. customThe mixture was purified by column chromatography

Sources & evidence

ORD record
ord-11975f29957c4fe1b919df806519568c
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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