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An improved synthesis of 4-aminobutanenitrile from 4-azidobutanenitrile and comments on room temperature stability

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dc.contributor.authorCapon, P.K.
dc.contributor.authorAvery, T.D.
dc.contributor.authorPurdey, M.S.
dc.contributor.authorAbell, A.D.
dc.date.issued2021
dc.description.abstract4-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.
dc.description.statementofresponsibilityPatrick K. Capon, Thomas D. Avery, Malcolm S. Purdey and Andrew D. Abell
dc.identifier.citationSynthetic Communications, 2021; 51(3):428-436
dc.identifier.doi10.1080/00397911.2020.1832527
dc.identifier.issn0039-7911
dc.identifier.issn1532-2432
dc.identifier.orcidCapon, P.K. [0000-0002-7396-5757]
dc.identifier.orcidAvery, T.D. [0000-0001-6882-5461]
dc.identifier.orcidPurdey, M.S. [0000-0002-5063-8972]
dc.identifier.orcidAbell, A.D. [0000-0002-0604-2629]
dc.identifier.urihttp://hdl.handle.net/2440/129887
dc.language.isoen
dc.publisherTaylor & Francis
dc.relation.granthttp://purl.org/au-research/grants/arc/CE140100003
dc.rights© 2020 Taylor & Francis Group, LLC.
dc.source.urihttps://doi.org/10.1080/00397911.2020.1832527
dc.subjectAminonitriles; nuclear magnetic resonance spectroscopy; stability; staudinger reduction
dc.titleAn improved synthesis of 4-aminobutanenitrile from 4-azidobutanenitrile and comments on room temperature stability
dc.typeJournal article
pubs.publication-statusPublished

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