4-(5-Nitro-thiophen-2-yl)-butyric acid methyl ester → 4-(5-Amino-thiophen-2-yl)-butyric acid methyl ester

HRID 1611492ノート

反応式

HRID 1611492 の反応式
[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH2:5][CH2:6][C:7]1[S:8][C:9]([N+:12]([O-])=O)=[CH:10][CH:11]=1>C(OCC)(=O)C.CO.[OH-].[Pd+2].[OH-]>[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH2:5][CH2:6][C:7]1[S:8][C:9]([NH2:12])=[CH:10][CH:11]=1

参加物

5

反応物 1

HCID 692334004-(5-Nitro-thiophen-2-yl)-butyric acid methyl ester

生成物 1

HCID 692355624-(5-Amino-thiophen-2-yl)-butyric acid methyl ester収率 66.2%

試薬・触媒・溶媒 3

HCID 9942167Palladium hydroxide触媒HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 4-(5-nitro-thiophen-2-yl)-butyric acid methyl ester (2.29 g, 10.0 mmol) and palladium hydroxide (500 mg, 20% on carbon) in 30 mL of ethyl acetate and 30 mL of methanol is hydrogenated at 50 psi for 48 hours. The reaction mixture is filtered and concentrated. The residue is purified by flash column chromatography eluting with 1:3 ethyl acetate:hexane to provide 1.32 g of 4-(5-amino-thiophen-2-yl)-butyric acid methyl ester as a dark oil; 1H NMR (DMSO-d6) δ 1.74 (m, 2H), 2.38 (m, 2H), 2.54 (m, 2H), 3.59 (s, 3H), 5.66 (d, J=3 Hz, 1H), 6.24 (d, J=3 Hz, 1H); MS 200.2 (M+H)+.

後処理

  1. filtrationThe reaction mixture is filtered
  2. concentrationconcentrated
  3. customThe residue is purified by flash column chromatography
  4. washeluting with 1:3 ethyl acetate

出典と根拠

ORDレコード
ord-93728a921a6f4cff8cd5aac40a9f16f2
出典データセット
uspto-grants-2006_01
特許番号
US06987116B2

反応ノート

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