A scalable asymmetric synthesis of (R)-2-amino-1-(3-pyridinyl) ethanol dihydrochloride via an oxazaborolidine catalyzed borane reduction

J Duquette, M Zhang, L Zhu…

Index: Duquette, Jason; Zhang, Mingbao; Zhu, Lei; Reeves, Raymond S. Organic Process Research and Development, 2003 , vol. 7, # 3 p. 285 - 288

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Citation Number: 28

Abstract

This report describes a scalable process for the asymmetric synthesis of (R)-2-amino-1-(3- pyridinyl) ethanol dihydrochloride. The stereochemistry of the product is set via a reduction of 3-chloroacetyl pyridine with 2 equiv of borane-dimethyl sulfide and a catalytic amount of an in situ generated oxazaborolidine. The enantiomeric excess (ee) of the reductive step depends on the addition rate of the substrate and the temperature. The authors ...