HCID 19870577, compound → HCID 19870615, compound

HRID 330186Notes

Reaction equation

HRID 330186 reaction equation
[C:1](/[C:4](/[CH3:31])=[CH:5]/[C:6]1[CH:14]=[C:13]2[C:9]([C:10]([CH2:28][CH2:29][CH3:30])=[CH:11][N:12]2[CH2:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=2[O:26][CH3:27])=[CH:8][CH:7]=1)([OH:3])=[O:2]>[Pd].O1CCCC1>[C:1]([CH:4]([CH3:31])[CH2:5][C:6]1[CH:14]=[C:13]2[C:9]([C:10]([CH2:28][CH2:29][CH3:30])=[CH:11][N:12]2[CH2:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=2[O:26][CH3:27])=[CH:8][CH:7]=1)([OH:3])=[O:2]

Participants

4

Reactant 1

HCID 19870577HCID 19870577, compound

Product 1

HCID 19870615HCID 19870615, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Methyl E-4-[6-(2-carboxyprop-1-enyl)-3-propylindol-1-ylmethyl]-3-methoxybenzoate (1.15 g) with palladium on carbon (10% w/w, 0.2 g) in dry tetrahydrofuran (50 ml) was hydrogenated at 2.0 bar. The mixture was filtered through a pad of diatomaceous earth and evaporated to give methyl 4-[6-(2-carboxypropyl)-3-propylindol-1-ylmethyl]-3-methoxybenzoate (1.12 g, 97%) as an oil; partial NMR (300 MHz, DMSO-d6): 0.93(t, 3H, CH2CH3), 0.98(d, 3H, CH(CH3)), 1.63(m, 2H, CH2CH3), 2.60(m, 4H, CH2CH2CH3, CHCH2), 2.96(m, 1H, CH(CH3)), 3.82(s, 3H, OCH3), 3.95(s, 3H, OCH3), 5.31(s, 2H, NCH2).

Workup

  1. filtrationThe mixture was filtered through a pad of diatomaceous earth
  2. customevaporated

Sources & evidence

ORD record
ord-760cbfbc604448d8b308bed40d9a810c
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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