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

HRID 2117523

反応式

HRID 2117523 の反応式
[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

参加物

7

反応物 2

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

生成物 2

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

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-120b5c5a44184a788669a7139fadc03c
出典データセット
uspto-grants-2008_10
特許番号
US07442702B2

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