title: A simple, scalable synthetic route to (+)- and (-)-pseudoephenamine.
abstract: A three-step synthesis of pseudoephenamine suitable for preparing multigram amounts of both enantiomers of the auxiliary from the inexpensive starting material benzil is described. The sequence involves synthesis of the crystalline monomethylimine derivative of benzil, reduction of that substance with lithium aluminum hydride, and resolution of pseudoephenamine with mandelic acid.
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University , Cambridge, Massachusetts 02138, United States.
authors.forename: Kevin T
authors.initials: KT
authors.lastname: Mellem
authors.forename: Andrew G
authors.initials: AG
authors.lastname: Myers
mesh_terms: D000661:Amphetamine / Q000138:chemical synthesis* / Q000737:chemistry; D000662:Amphetamines / Q000138:chemical synthesis* / Q000737:chemistry; D001593:Benzyl Compounds / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000662:Amphetamines; D001593:Benzyl Compounds; C587965:pseudoephenamine; D000661:Amphetamine