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

摘要

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.