Nitrile reduction in the presence of Boc-protected amino groups by catalytic hydrogenation over palladium-activated Raney-nickel was written by Klenke, Burkhard;Gilbert, Ian H.. And the article was included in Journal of Organic Chemistry in 2001.Electric Literature of C20H34N4O4 The following contents are mentioned in the article:
Nitriles NCCH2CH2NX-R-NXCH2CH2CN [R = (CH2)n, 1,2-cyclohexyl, 1,4-cyclohexyl, CHMeCH2, X = Boc, n = 4, 7, 9, 12; R = 1,2-Ph, 1,3-Ph, 1,4-Ph, X = H] are reduced to primary amines in the presence of N-tert-butoxycarbonyl (Boc) groups. E.g., NCCH2CH2N(Boc)(CH2)4N(Boc)CH2CH2CN in absolute ethanol and THF was stirred with a mixture of Pd/C and Raney nickel and sodium hydroxide; the mixture was shaken for 8 h under 45 psi of hydrogen and worked up to give H2N(CH2)3N(Boc)(CH2)4N(Boc)(CH2)3NH2 in 84% yield. The reduction can be carried out under atm. H2 pressure using com. avail. catalysts. Both Boc groups and aromatic moieties present in the starting material are well tolerated under the mild optimized conditions. This study involved multiple reactions and reactants, such as Di-tert-butyl butane-1,4-diylbis((2-cyanoethyl)carbamatE) (cas: 194808-59-8Electric Literature of C20H34N4O4).
Di-tert-butyl butane-1,4-diylbis((2-cyanoethyl)carbamatE) (cas: 194808-59-8) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Electric Literature of C20H34N4O4
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts