tert-Butyl 2-{[3-(cyanomethyl)benzyl]oxy}ethylcarbamate → tert-Butyl 2-{[3-(2-aminoethyl)benzyl]oxy}ethylcarbamate

HRID 2228775Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2228775
[C:1]([CH2:3][C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[CH2:7][O:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])#[N:2]>N.[Ni]>[NH3:2].[NH2:2][CH2:1][CH2:3][C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[CH2:7][O:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:15])[CH3:16]

Komponenten

5

Edukt 1

HCID 18470797tert-Butyl 2-{[3-(cyanomethyl)benzyl]oxy}ethylcarbamate

Produkt 2

HCID 222AmmoniaHCID 18470932tert-Butyl 2-{[3-(2-aminoethyl)benzyl]oxy}ethylcarbamateAusbeute 161,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 222AmmoniaLösungsmittel

Versuchsvorschrift

Raney® nickel (170 mg) was added to a solution of tert-butyl 2-{[3-(cyanomethyl)benzyl]oxy}ethylcarbamate (preparation 104) (654 mg, 2.26 mmol) in ethanolic ammonia solution (15 ml), and the mixture hydrogenated at 60 psi and room temperature for 24 hrs. The reaction mixture was filtered through Arbocel®, and the filtrate evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (90:10:1) to afford the title compound, (536 mg, 80%).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through Arbocel®
  2. customthe filtrate evaporated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-a812d3769a7d4bc7824a5a43e3dd7ee2
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06417203B1

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