title: Concise, Protecting-Group-Free Synthesis of (+)-Nemonapride via Eu(OTf)3-Catalyzed Aminolysis of 3,4-Epoxy Alcohol.
abstract: A concise, protecting-group-free synthesis of the antipsychotic agent (+)-nemonapride has been achieved featuring a europium(III) trifluoromethanesulfonate (Eu(OTf)3)-catalyzed C4 selective aminolysis of a 3,4-epoxy alcohol by benzylamine and an expedient use of the resulting 4-benzylamino-1,3-diol product for constructing the pyrrolidine skeleton.
authors.affiliation: Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University.
authors.forename: Shun-Ichiro
authors.initials: SI
authors.lastname: Uesugi
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Sasano
authors.forename: Shogo
authors.initials: S
authors.lastname: Matsui
authors.forename: Naoki
authors.initials: N
authors.lastname: Kanoh
authors.forename: Yoshiharu
authors.initials: Y
authors.lastname: Iwabuchi
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D001549:Benzamides / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: C000613867:3,4-epoxy alcohol; D000438:Alcohols; D000588:Amines; D001549:Benzamides; D004852:Epoxy Compounds; D008698:Mesylates; C012077:trifluoromethanesulfonic acid; C030265:nemonapride