Stereoselectivity of (−)-(1R,2S)-2-methylamino-1-phenyl-propan-1-ol preparation

Authors: Astrová, Martina; Kurc, Ladislav; Červený, Libor

Source: Research on Chemical Intermediates, Volume 33, Number 7, 2007 , pp. 663-673(11)

Buy & download fulltext article:

Price: $35.00 plus tax (Refund Policy)

Abstract:

Stereoselectivity of reductive amination of (R)-1-hydroxy-1-phenylpropan-2-one by methylamine was studied. From the four isomers possible, only two are produced by this reaction. These are marked as (-)-(1R,2S)-ephedrine (desired product) and (+)-(1S,2R)-ephedrine. The reaction stereoselectivity depends both on the type of the catalyst and reaction conditions. The most suitable type is the supported platinum. However, this catalyst rapidly deactivates. With a decreasing activity of Pt catalyst, the stereoselectivity decreases. It is also decreased during the production of the second liquid phase (water) in the reaction mixture.

Keywords: STEREOSELECTIVITY; EPHEDRINE; HYDROGENATION; LIQUID PHASE

Document Type: Research article

DOI: http://dx.doi.org/10.1163/156856707781749892

Affiliations: 1: Department of Organic Technology, Institute of Chemical Technology in Prague, Technická 5, 166 28 Praha 6, Czech Republic

Publication date: 2007-07-01