PRODUCTION OF OPTICALLY ACTIVE 3-AMINO-2-BUTANOL DERIVATIVE FROM 3-AMINO-2-HYDROXYBUTYRIC ESTER DERIVATIVE AS STARTING MATERIAL

摘要

PURPOSE:To obtain an optically active 3-amino-2-butanol derivative important as a medicinal intermediate through four steps via new intermediates using as starting material a readily available optically active 3-amino-2-hydroxybutyric ester. CONSTITUTION:An optically active 3-amino-2-hydroxybutyric ester of formula I (R<4> is phenyl or cyclohexyl; R<2> and R<3> are each H or a protecting group; R us H, a 1-4C alkyl or allyl; the configurations for *1 and *2 are S- and R-configurations, respectively) to produce an optically active 3-amino-1,2- butanediol derivative of formula II. Second, the primary hydroxyl group of the compound of formula II is sulfonated into a new optically active 3-amino-1- sulfonyloxy-2-butanol derivative of formula III (R<5> is a lower alkyl or an aryl). Third, the compound of formula III is epoxidized through its 1,3-elimination to produce an optically active 3-amino-1-butene oxide derivative of formula IV. Finally, an organometallic reagent is subjected to site-selective nucleophilic substitution reaction with the compound of formula IV, thus obtaining the aimed compound of formula V.