(R)-3-(1-azidoethyl)-5-(prop-1-en-2-yl)pyridine → (R)-1-(5-(prop-1-en-2-yl)pyridin-3-yl)ethanamine
Reaktionsgleichung
[N:1]([C@@H:4]([C:6]1[CH:7]=[N:8][CH:9]=[C:10]([C:12]([CH3:14])=[CH2:13])[CH:11]=1)[CH3:5])=[N+]=[N-]>CO.Cl.[Pd]>[CH2:13]=[C:12]([C:10]1[CH:11]=[C:6]([C@H:4]([NH2:1])[CH3:5])[CH:7]=[N:8][CH:9]=1)[CH3:14]Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
To a stirred solution of (R)-3-(1-azidoethyl)-5-(prop-1-en-2-yl)pyridine (340 mg) in MeOH.HCl (1.25M, 10 mL) was added 10% Pd/C (50 mg) and stirred under hydrogen atmosphere for 12 h. The catalyst was filtered off and the residue was dissolved in 5 mL of 25% aqueous NH3 and extracted with CHCl3 and the organic layer was washed with brine, dried with Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (10% MeOH/90% CHCl3 spiked with 0.25% of Et3N) to provide 246 mg of (R)-1-(5-(prop-1-en-2-yl)pyridin-3-yl)ethanamine.