Nitrile reduction in the presence of Boc-protected amino groups by catalytic hydrogenation over palladium-activated Raney-nickel

B Klenke, I H Gilbert

    Research output: Contribution to journalArticle

    33 Citations (Scopus)


    Polyamines have attracted considerable interest, especially after the discovery of their ubiquitous presence in living cells and their involvement in many metabolic processes.1 As part of a program to synthesize homologues and derivatives of naturally occurring polyamines, we utilized the reduction of nitriles in the presence of Boc-protected amino groups. Nitriles are a versatile synthon for amines in organic chemistry and can be prepared by a variety of methods.2 Furthermore, there are a number of methods available for the subsequent reduction to amines.2 Catalytic hydrogenation3 has been carried out using Raney-nickel,4,5 Pd(OH)2/C,6 Pd/C,7 or PtO28 as catalyst. Alternatively, complex metal hydrides,9 especially NaBH4 + CoCl2·6H2O,10 NaBH4 + NiCl2·6H2O,11 and LiAlH4 variations,12 have been used successfully to achieve the nitrile-amine transformation. Here we report the use of palladium activated Raney-nickel for the reduction of nitriles to primary amines for cases in which other methods were unsuccessful.
    Original languageEnglish
    Pages (from-to)2480-2483
    Number of pages4
    JournalJournal of Organic Chemistry
    Issue number7
    Publication statusPublished - 6 Apr 2001

    Cite this