Synfacts 2009(12): 1309-1309  
DOI: 10.1055/s-0029-1218411
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (R)-Orphenadrine

Contributor(s): Philip Kocienski
D. Sälinger, R. Brückner*
Universität Freiburg, Germany
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Publikationsverlauf

Publikationsdatum:
20. November 2009 (online)

Significance

Orphenadrine is an antihistamine and anticholinergic drug. Sälinger and Brückner report a short synthesis of (R)-orphenadrine that features the first asymmetric ligand-accelerated halogen-metal exchange in which the pro-S bromoarene of the substrate B reacts faster than the pro-R bromoarene leading to kinetic selection for the organomagnesium derivative D. Simple protonolysis of D gave the key intermediate E.