Capon, P.K.Avery, T.D.Purdey, M.S.Abell, A.D.2021-03-102021-03-102021Synthetic Communications, 2021; 51(3):428-4360039-79111532-2432http://hdl.handle.net/2440/1298874-Aminobutanenitrile (1) is an important synthetic intermediate for neurological disorder therapeutics including Parkinson’s and Alzheimer’s diseases, and is an industrial precursor to pyrroline and pyrrolidine. Synthesis of 1 by Co(II) catalyzed reduction of 4-azidobutanenitrile (2) with NaBH4, or by a one-pot Staudinger reduction of 2 in THF, was low yielding. 1H-NMR analysis of the Staudinger reduction revealed the formation of iminophosphorane intermediate (3) after 22 h at rt, and that increasing the reaction temperature from rt to 40 °C promoted hydrolysis of 3 to 1. A modified Staudinger reduction of 2 involving pyridine as solvent, addition of water 3 h after triphenylphosphine, and a temperature increase to 40 °C, gave rise to 1 in 69% yield. 1 is unstable at rt, thus the hydrochloride salt of 1 (1⋅HCl) was prepared by bubbling HCl(g) through a solution of 1 in chloroform. 1⋅HCl is stable at rt and is hence the preferred form for storage.en© 2020 Taylor & Francis Group, LLC.Aminonitriles; nuclear magnetic resonance spectroscopy; stability; staudinger reductionJournal article100003163410.1080/00397911.2020.18325270006010313000012-s2.0-85097931083559354Capon, P.K. [0000-0002-7396-5757]Avery, T.D. [0000-0001-6882-5461]Purdey, M.S. [0000-0002-5063-8972]Abell, A.D. [0000-0002-0604-2629]