methyl E-4-[5-(2-carboxy-1-propenyl)-1-methylindol-3-ylmethyl]-3-methoxybenzoate → Methyl 4-[5-(2-carboxypropyl)-1-methylindol-3-ylmethyl]-3-methoxybenzoate
Reaction equation
[C:1](/[C:4](/[CH3:29])=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH3:15])[CH:10]=[C:9]2[CH2:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][C:18]=1[O:27][CH3:28])([OH:3])=[O:2]>[Pd].O1CCCC1>[C:1]([CH:4]([CH3:29])[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH3:15])[CH:10]=[C:9]2[CH2:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][C:18]=1[O:27][CH3:28])([OH:3])=[O:2]Participants
Procedure
Palladium on carbon (10% w/w, 0.3 g) was added to a solution of methyl E-4-[5-(2-carboxy-1-propenyl)-1-methylindol-3-ylmethyl]-3-methoxybenzoate (4.14 g) in redistilled tetrahydrofuran (75 ml) in a hydrogenation bottle. The mixture was hydrogenated at 2.7 bar for 4 hr. The catalyst was removed by filtration through diatomaceous earth, the filter pad was washed with tetrahydrofuran, and the filtrate evaporated. The residue was crystallized from methanol to give methyl 4-[5-(2-carboxypropyl)-1-methylindol-3-ylmethyl]-3-methoxybenzoate (3.82 g, 92%) as white crystals; mp 149°-151°; partial NMR (250 MHz, DMSO-d6) 1.0(d, CHCH3), 2.60(m, 2H, CHCH2Ar), 3.34(m, 1H, CHCH2), 3.67(s, 3H), 3.83(s, 3H), 3.91(s, 3H), 3.99(s, 2H, ArCH2Ar'), 12.05(s, 1H, COOH).
Workup
- customThe catalyst was removed by filtration through diatomaceous earth
- washthe filter pad was washed with tetrahydrofuran
- customthe filtrate evaporated
- customThe residue was crystallized from methanol
Sources & evidence
- ORD record
- ord-8b0c1a10bfd04ffebff639d65d1dd234
- Source dataset
- uspto-grants-1990_01
- Patent number
- US04894386
Reaction notes
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