methyl 5-[(E)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethenyl]-2-(propan-2-yloxy)pyridine-4-carboxylate → methyl 5-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-2-(propan-2-yloxy)pyridine-4-carboxylate
Reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1/[CH:12]=[CH:13]/[C:14]1[C:15]([C:24]([O:26][CH3:27])=[O:25])=[CH:16][C:17]([O:20][CH:21]([CH3:23])[CH3:22])=[N:18][CH:19]=1>C1COCC1.CCO.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[O:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[N:3]1[CH2:12][CH2:13][C:14]1[C:15]([C:24]([O:26][CH3:27])=[O:25])=[CH:16][C:17]([O:20][CH:21]([CH3:23])[CH3:22])=[N:18][CH:19]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of methyl 5-[(E)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethenyl]-2-(propan-2-yloxy)pyridine-4-carboxylate (112b, 1.56 g, 4.26 mmol) in THF/EtOH (25 mL/5 mL) was hydrogenated on an H-Cube with Wilkinson's catalyst (10 bar, 75° C., 18 hours). The solvent was removed under vacuum and the resulting gum was purified by column chromatography (0-50% ethyl acetate/heptanes) to give methyl 5-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-2-(propan-2-yloxy)pyridine-4-carboxylate (112c, 0.63 g, 40%) as a white solid.
Workup
- customThe solvent was removed under vacuum
- customthe resulting gum was purified by column chromatography (0-50% ethyl acetate/heptanes)
Sources & evidence
- ORD record
- ord-f9aed2b567c34c668c8349b55dd254bb
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09040515B2
Reaction notes
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