Regioisomerism in the Synthesis of a Chiral Aminotetralin Drug Compound: Unraveling Mechanistic Details and Diastereomer-Specific In-Depth NMR Investigations

P Schuisky, HJ Federsel, W Tian

Index: Schuisky, Peter; Federsel, Hans-Juergen; Tian, Wei Journal of Organic Chemistry, 2012 , vol. 77, # 13 p. 5503 - 5514

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Citation Number: 3

Abstract

During chemical process development of a novel 2-aminotetralin derivative intended for use as an antidepressant, scrutiny of the byproduct present in the drug molecule revealed a set of regioisomers. Detailed studies showed that this impurity issue originated from an early synthetic step in which a brominated tetralone motif was generated in a ring-closing protocol. It was found that this reaction was accompanied by a migration of the aromatic ...