tert-butyl N-methyl-N-[2-(2-nitrophenyl)ethyl]carbamate → N-(2-(2-aminophenyl)ethyl)-N-methylcarbamic acid tert-butyl ester

HRID 650822Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 650822
[C:1]([O:5][C:6](=[O:20])[N:7]([CH3:19])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-])=O)([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:20])[N:7]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH2:16])[CH3:19])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 1

HCID 20677535tert-butyl N-methyl-N-[2-(2-nitrophenyl)ethyl]carbamate

Produkt 1

HCID 10800697N-(2-(2-aminophenyl)ethyl)-N-methylcarbamic acid tert-butyl esterAusbeute 87,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

N-Methyl-N-(2-(2-nitrophenyl)ethyl)carbamic acid tert-butyl ester (924 mg, 3.3 mmol) was dissolved in ethanol (60 ml). 10% palladium on carbon (200 mg) was added. The mixture was hydrogenated at room temperature at 1 atmosphere for 16 h. The catalyst was filtered off through a plug of celite. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (60 g), using ethyl acetate/heptane (1:2) as eluent, to give 723 mg of N-(2-(2-aminophenyl)ethyl)-N-methylcarbamic acid tert-butyl ester.

Aufarbeitung

  1. filtrationThe catalyst was filtered off through a plug of celite
  2. customThe solvent was removed in vacuo
  3. customThe crude product was purified by flash chromatography on silica (60 g)

Quellen und Nachweise

ORD-Eintrag
ord-2fa447c15cd74f309224f21f5b02f82a
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06274584B1

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