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

HRID 735648Notes

Reaction equation

HRID 735648 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-f1928c0821214055bc885c954c8a8cde
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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