3-(4-Azidomethyl-2-methyl-phenyl)-propionic Acid Methyl Ester → 3-(4-Aminomethyl-2-methyl-phenyl)-propionic Acid Methyl Ester

HRID 1785216Notes

Reaction equation

HRID 1785216 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][N:13]=[N+]=[N-])=[CH:8][C:7]=1[CH3:16].[H][H]>CCO.[Pd]>[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][NH2:13])=[CH:8][C:7]=1[CH3:16]

Participants

5

Reactant 2

HCID 574319823-(4-Azidomethyl-2-methyl-phenyl)-propionic Acid Methyl EsterHCID 178418361HCID 178418361, compound

Product 1

HCID 574319803-(4-Aminomethyl-2-methyl-phenyl)-propionic Acid Methyl EsterYield 78.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-(4-Azidomethyl-2-methyl-phenyl)-propionic acid methyl ester (0.20 g, 0.86 mmol) and 5% Pd/C (32 mg) in EtOH (50 mL) is exposed to a hydrogen atmosphere (60 psi) at RT overnight. Upon filtering the mixture through Celite, the filtrate is concentrated to yield the title compound (0.14 g, 78%). The material is used without further purification.

Workup

  1. filtrationUpon filtering the mixture through Celite
  2. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-94a6019a1fd24619b8cf383a7ae1c3be
Source dataset
uspto-grants-2009_03
Patent number
US07504433B2

Reaction notes

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