Synthesis of the beta(3)-Adrenergic Receptor Agonist Solabegron and Analogous N-(2-Ethylamino)-beta-amino Alcohols from O-Acylated Cyanohydrins - Expanding the Scope of Minor Enantiomer Recycling
2015 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 80, no 5, 2937-2941 p.Article in journal (Refereed) Published
A novel methodology to produce highly enantioenriched N-(2-ethylamino)-beta-amino alcohols was developed. These compounds were obtained from O-(alpha-bromoacyl) cyanohydrins, which were synthesized by the minor enantiomer methodology employing a Lewis acid and a biocatalyst, followed by nucleophilic substitution with amines and reduction. The importance of the developed methodology was demonstrated by completing a highly enantioselective total synthesis of the beta(3)-adrenergic receptor agonist Solabegron.
Place, publisher, year, edition, pages
2015. Vol. 80, no 5, 2937-2941 p.
IdentifiersURN: urn:nbn:se:kth:diva-163973DOI: 10.1021/acs.joc.5b00322ISI: 000350841600054PubMedID: 25689345ScopusID: 2-s2.0-84924326489OAI: oai:DiVA.org:kth-163973DiVA: diva2:810597
FunderSwedish Research Council, 621-2012-3391
QC 2015045072015-05-072015-04-132015-09-08Bibliographically approved