Convenient synthesis of (2R)- and (2S)-2-(1-methylethyl)-5-oxo-2-phenylpentanenitrile, intermediates in the preparation of phenylalkylamine calcium channel blockers
- 1 January 1996
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 23,p. 2845-2850
- https://doi.org/10.1039/p19960002845
Abstract
The multigram synthesis of (2S)- and (2R)-2-(1-methylethyl)-5-oxo-2-phenylpentanenitriles 9a and 9b is described, using either (4R)-2,2-dimethyl-1,3-dioxolan-4-ylmethanol or (2R)-butane-1,2,4-triol as chiral auxiliary. The configuration of an intermediate dioxolane 10b is assigned by X-ray crystallography. The synthetic utility of the aldehydes is demonstrated by conversion to both enantiomers of the calcium antagonist noremopamil in >98% enantiomeric excess(ee). The enantiomeric purity of the final amines is assayed by 1H NMR spectroscopy in the presence of the chiral solvating agent (1R)-(–)-2,2,2-trifluoro-1-(9-anthryl)ethanol.Keywords
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