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

HRID 735648Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 735648
[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

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-f1928c0821214055bc885c954c8a8cde
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592331B2

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