title: Synthesis of the β3-adrenergic receptor agonist solabegron and analogous N-(2-ethylamino)-β-amino alcohols from O-acylated cyanohydrins - expanding the scope of minor enantiomer recycling.
abstract: A novel methodology to produce highly enantioenriched N-(2-ethylamino)-β-amino alcohols was developed. These compounds were obtained from O-(α-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 β3-adrenergic receptor agonist Solabegron.
authors.affiliation: KTH Royal Institute of Technology , Department of Chemistry, Organic Chemistry, SE-10044 Stockholm, Sweden.
authors.forename: Robin
authors.initials: R
authors.lastname: Hertzberg
authors.forename: Guillermo
authors.initials: G
authors.lastname: Monreal Santiago
authors.forename: Christina
authors.initials: C
authors.lastname: Moberg
mesh_terms: D000215:Acylation; D000322:Adrenergic Agonists / Q000138:chemical synthesis / Q000737:chemistry; D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000814:Aniline Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001565:Benzoates / Q000138:chemical synthesis* / Q000737:chemistry; D055162:Biocatalysis; D001713:Biphenyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D058116:Lewis Acids / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000322:Adrenergic Agonists; D000605:Amino Alcohols; D000814:Aniline Compounds; D001565:Benzoates; D001713:Biphenyl Compounds; D058116:Lewis Acids; D009570:Nitriles; C430593:cyanohydrin; C523977:solabegron