(<i>R</i>)-<i>N</i>-Benzyl-<i>N</i>-(1-phenylethyl)cyclohexanamine

Abstract

The preparation and characterization of a new chiral tertiary dibenzylamine are described. These molecules are well known in the literature for their high neuropharmacological potential. The general synthetic pathway is based on asymmetric Aza–Michael addition of chiral (R)-N-benzyl-N-(α-methylbenzyl)amide to methyl cyclohex-1-en-carboxilate obtaining the β-amino ester, followed by carboxylic acid hydrolysis and subsequent Barton descarboxylation. Interestingly, it is a general synthetic procedure of a wide range of chiral amines by careful choice of insaturated esters and alkylation of the chiral enolate in the initial reaction. The new tertiary dibenzylamine molecule is fully characterized by NMR Spectroscopy (1H and 13C), as well by High-Resolution Mass Spectrometry and Infrared Spectroscopy.

Keywords

• tertiary dibenzylamine
• chiral lithium amide
• neurodegenerative disorders
• radical decarboxylation