tert-Butyl N-[3-(cyanomethyl)benzyl]-N-methylcarbamate → tert-Butyl N-[3-(2-aminoethyl)benzyl]-N-methylcarbamate

HRID 567806Notizen

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Reaktionsgleichung von HRID 567806
[C:1]([O:5][C:6](=[O:19])[N:7]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][C:17]#[N:18])[CH:11]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]>C(O)C.N.[Ni]>[NH2:18][CH2:17][CH2:16][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=1)[CH2:9][N:7]([CH3:8])[C:6](=[O:19])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4]

Komponenten

5

Edukt 1

HCID 18470858tert-Butyl N-[3-(cyanomethyl)benzyl]-N-methylcarbamate

Produkt 1

HCID 18470795tert-Butyl N-[3-(2-aminoethyl)benzyl]-N-methylcarbamateAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 935NickelKatalysatorHCID 222AmmoniaLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

tert-Butyl-N-[3-(cyanomethyl)benzyl]-N-methylcarbamate (preparation 14) (3 g, 11.5 mmol, slightly impure) was dissolved in ethanol saturated with NH3 (300 ml), treated with Raney® Nickel (500 mg) and stirred under a hydrogen atmosphere (60 psi, room temperature, 18 hr). The catalyst was removed by filtration under nitrogen, the solvent evaporated to dryness and the resultant crude product purified by chromatography (SiO2, gradient elution with 100% CH2Cl2; 95:5 CH2Cl2:MeOH; 90:10 CH2Cl2:MeOH) to give the desired product (2.40 g, 78%). 1H NMR (CDCl3) δ 1.20 (s, 2H), 1.50 (s, 9H), 2.70-2.90 (m, 5H), 3.00 (s, 2H), 4.20 (s, br, 2H), 7.05 (s, br, 3H), 7.25 (s, br, 1H). LRMS m/z=265.1 (M+1)+.

Aufarbeitung

  1. customThe catalyst was removed by filtration under nitrogen
  2. customthe solvent evaporated to dryness
  3. customthe resultant crude product purified by chromatography (SiO2, gradient elution with 100% CH2Cl2; 95:5 CH2Cl2:MeOH; 90:10 CH2Cl2:MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-20cb947ef3b7437f862d0e1e441f9ac8
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06180627B2

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