Ammonium Hydroxide → 3-(3-Aminomethyl-phenyl)-2-methyl-propionic acid methyl ester

HRID 2300476

Reaction equation

HRID 2300476 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH:4]([CH3:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]#[N:13])[CH:7]=1.[OH-].[NH4+]>[Pd].CO.CCOC(C)=O>[NH4+:13].[OH-:2].[CH3:1][O:2][C:3](=[O:15])[CH:4]([CH3:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][NH2:13])[CH:7]=1

Participants

7

Reactant 2

HCID 14923Ammonium HydroxideHCID 545230243-(3-Cyano-phenyl)-2-methyl-propionic acid methyl ester

Product 2

HCID 14923Ammonium HydroxideHCID 537025913-(3-Aminomethyl-phenyl)-2-methyl-propionic acid methyl esterYield 144.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(3-cyano-phenyl)-2-methyl-propionic acid methyl ester of Step B (62 mg, 0.30 mmol) and palladium on carbon (10%, 50 mg) in MeOH (10 mL), EtOAc (10 mL), and ammonium hydroxide (5 mL) was hydrogenated at 40 psi for 24 h. The catalyst was removed via filtration through Celite with the aid of MeOH. The solvent was removed in vacuo. Chromatography (1:1 hexanes:EtOAc to CH2Cl2:MeOH:NH4OH, 95:5:0.1) provided the title compound of Step C (45 mg). 1H NMR (400 MHz, CD3OD) δ 7.31-7.14 (m, 4H), 3.94 (s, 2H), 3.59 (s, 3H), 2.96 (m, 1H), 2.72 (m, 2H), 1.12 (d, 3H); MS 208 (M+1).

Workup

  1. customThe catalyst was removed via filtration through Celite with the aid of MeOH
  2. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4cd25948395f4170a4c3c07a08b319fe
Source dataset
uspto-grants-2002_12
Patent number
US06498172B1

Linked notes

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