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

HRID 735648노트

반응식

HRID 735648 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 23925Iron촉매HCID 176Acetic Acid용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-f1928c0821214055bc885c954c8a8cde
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592331B2

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