HCID 57170316, compound → HCID 19870604, compound

HRID 330146Notes

Reaction equation

HRID 330146 reaction equation
[CH:1]1([CH2:6][NH:7][C:8]([CH2:10][C:11]2[CH:19]=[C:18]3[C:14]([C:15]([CH:36]=[CH:37][C:38]([O:40][CH3:41])=[O:39])=[CH:16][N:17]3[CH2:20][C:21]3[CH:33]=[CH:32][C:24]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:23][C:22]=3[O:34][CH3:35])=[CH:13][CH:12]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>CO.[Pd]>[CH:1]1([CH2:6][NH:7][C:8]([CH2:10][C:11]2[CH:19]=[C:18]3[C:14]([C:15]([CH2:36][CH2:37][C:38]([O:40][CH3:41])=[O:39])=[CH:16][N:17]3[CH2:20][C:21]3[CH:33]=[CH:32][C:24]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:23][C:22]=3[O:34][CH3:35])=[CH:13][CH:12]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 57170316HCID 57170316, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19870604HCID 19870604, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of t-butyl 4-[6-(cyclopentylmethylcarbamoyl)methyl-3-(2-methoxycarbonylvinyl)indol-1-ylmethyl]-3-methoxybenzoate (0.54 g) in methanol (20 ml) was treated with 10% palladium on carbon (0.13 g) and shaken under 3.45 bars of hydrogen for 18 hours. The catalyst was removed by filtration through diatomaceous earth, and the filtrate was evaporated to give t-butyl 4-[6-(cyclopentylmethylcarbamoyl)methyl-3-(2-methoxycarbonylethyl)indol-1-ylmethyl]-3-methoxybenzoate (0.45 g, 84%) as a white foam; partial NMR (80 MHz, CDCl3): 1.54(s, 9H, C(CH3)3), 2.69(t, 2H, COCH2), 3.62(s, 2H, COCH2Ar), 3.65(s, 3H, CO2CH3), 3.93(s, 3H, OCH3), 5.25(s, 2H, NCH2Ar).

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-6a6901cb26c849718c8e46b4f69ecc3c
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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