Ethanol → (S)-benzyl 1-(3-aminophenyl)ethylcarbamate

HRID 735648ノート

反応式

HRID 735648 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([C@@H:10]([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:11])[CH:7]=[CH:8][CH:9]=1)([O-])=O.CCO.O>[Fe].CC(O)=O>[NH2:1][C:4]1[CH:5]=[C:6]([C@@H:10]([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH3:11])[CH:7]=[CH:8][CH:9]=1

参加物

6

反応物 3

HCID 702EthanolHCID 962WaterHCID 57842774(S)-benzyl 1-(3-nitrophenyl)ethylcarbamate

生成物 1

HCID 57842795(S)-benzyl 1-(3-aminophenyl)ethylcarbamate収率 94%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 176Acetic Acid溶媒

実験手順

To a refluxing solution of 59A (1.7 g, 5.9 mmol), EtOH (60 mL), water (15 mL) and AcOH (4 mL) was added portion-wise Fe powder (1.6 g, 29.5 mmol) over 30 min. Mixture was heated for 45 min. before cooling to ambient temperature and filtering through celite. Filtration and concentration in vacuo afforded 59B (1.5 g, 94%) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.43 (d, J=6.59 Hz, 3 H) 5.00-5.17 (m, 2 H) 5.40 (d, J=7.47 Hz, 1 H) 6.53-6.60 (m, 2 H) 6.69 (d, J=7.47 Hz, 1 H) 7.11 (t, J=7.69 Hz, 1 H) 7.29-7.39 (m, 5 H).

後処理

  1. temperatureMixture was heated for 45 min.
  2. filtrationfiltering through celite
  3. filtrationFiltration and concentration in vacuo

出典と根拠

ORDレコード
ord-f1928c0821214055bc885c954c8a8cde
出典データセット
uspto-grants-2009_09
特許番号
US07592331B2

反応ノート

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