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

HRID 2117523

Reaktionsgleichung

Reaktionsgleichung von HRID 2117523
[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

Komponenten

7

Edukt 2

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

Produkt 2

HCID 14923Ammonium HydroxideHCID 537025913-(3-Aminomethyl-phenyl)-2-methyl-propionic acid methyl esterAusbeute 144,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-120b5c5a44184a788669a7139fadc03c
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07442702B2

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