5-(2-tert-butoxycarbonyl-vinyl)-1H-indole-2-carboxylic acid ethyl ester → 5-(2-tert-butoxycarbonyl-ethyl)-1H-indole-2-carboxylic acid ethyl ester

HRID 49056Notes

Reaction equation

HRID 49056 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([CH:15]=[CH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:10][CH:9]=2)=[O:5])[CH3:2]>C(OCC)(=O)C.CO.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([CH2:15][CH2:16][C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

5

Reactant 1

HCID 695871265-(2-tert-butoxycarbonyl-vinyl)-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 695871365-(2-tert-butoxycarbonyl-ethyl)-1H-indole-2-carboxylic acid ethyl esterYield 100.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-(2-tert-butoxycarbonyl-vinyl)-1H-indole-2-carboxylic acid ethyl ester (1.6 g, 5 mmol) in ethyl acetate (40 mL) and methanol (80 mL) was hydrogenated over 5% palladium on carbon (0.2 g) at room temperature for overnight. The catalyst was filtered off and the filtrate was concentrated to give 1.6 g (99%) of 5-(2-tert-butoxycarbonyl-ethyl)-1H-indole-2-carboxylic acid ethyl ester as a white solid. The solid was used in the next step without further purification.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-1a7d1f4f8d2a4f71924842c51bb55542
Source dataset
uspto-grants-2004_03
Patent number
US06706709B2

Reaction notes

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