Methyl 3-methoxy-4-[1-propyl-5-[3-(propylcarbamoyl)prop-1-enyl]indol-3-ylmethyl]benzoate → Methyl 3-methoxy-4-[1-propyl-5-[3-(propylcarbamoyl)propyl]indol-3-ylmethyl]benzoate
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([CH:23]=[CH:24][CH2:25][C:26](=[O:31])[NH:27][CH2:28][CH2:29][CH3:30])[CH:21]=2)[N:16]([CH2:32][CH2:33][CH3:34])[CH:15]=1)[C:6]([O:8][CH3:9])=[O:7]>[Pd].C(OCC)(=O)C.O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([CH2:23][CH2:24][CH2:25][C:26](=[O:31])[NH:27][CH2:28][CH2:29][CH3:30])[CH:21]=2)[N:16]([CH2:32][CH2:33][CH3:34])[CH:15]=1)[C:6]([O:8][CH3:9])=[O:7]Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
Palladium on carbon (0.055 g, 10% w/w) was added to a solution of methyl 3-methoxy-4-[1-propyl-5-[3-(propylcarbamoyl)prop-1-enyl]indol-3-ylmethyl]benzoate (0.545 g) in ethyl acetate (15 ml) and tetrahydrofuran (10 ml), and the mixture hydrogenated at atmospheric pressure for 6 hr. The catalyst was removed by filtration through diatomaceous earth, the filter cake washed with ethyl acetate, and the combined filtrate evaporated to give methyl 3-methoxy-4-[1-propyl-5-[3-(propylcarbamoyl)propyl]indol-3-ylmethyl]benzoate (0.52 g, 95%) as a white solid; mp 100°; partial NMR (300 MHz, DMSO-d6): 0.81(m, 6H, 2×CH3). 3.82(s, 3H, OCH3), 3.91(s, 3H, OCH3), 7.73(t, 1H, NH).
Workup
- customThe catalyst was removed by filtration through diatomaceous earth
- washthe filter cake washed with ethyl acetate
- customthe combined filtrate evaporated
Sources & evidence
- ORD record
- ord-ad3317eeacf443a8bf8347aef2c64997
- Source dataset
- uspto-grants-1990_01
- Patent number
- US04894386
Reaction notes
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