https://www.thevespiary.org/rhodium/Rhodium/chemistry/nitrile2amine.html#nabutanol (https://www.thevespiary.org/rhodium/Rhodium/chemistry/nitrile2amine.html#nabutanol)
Post 450229 (https://www.thevespiary.org/talk/index.php?topic=9087.msg45022900#msg45022900)
(Rhodium: "Catalytic Reduction of Nitriles and Oximes", Methods Discourse).Post 360373 (https://www.thevespiary.org/talk/index.php?topic=9486.msg36037300#msg36037300)
(Barium: "TMA-2 by low-pressure catalytic hydrogenation.", Methods Discourse), sort of hard to accept. No TLC was done on the final product to see how much secondary amine was in there, and an excess of base in the reaction was not used (just the base absorbed on the Ra-Ni).Post 465743 (missing)
(Rhodium: "NaBH4/NiCl2/Boc2O: Nitriles to N-Boc-Amines", Novel Discourse) - they cleverly use Boc2O to prevent the formation of any secondary amines. Boc2O is apparently not affected by the reduction system, but as soon as a primary amine is formed, it is acylated to the N-Boc carbamate, preventing any further dimerization. The N-Boc is then cleaved in nearly quantitative yield using HCl.