HCID 178498129, compound → HCID 67442141, compound

HRID 1801395Notes

Reaction equation

HRID 1801395 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-dbf4175080534e13ae74c2d70d931f05
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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