Convenient synthesis of (2R)- and (2S)-2-(1-methylethyl)-5-oxo-2-phenylpentanenitrile, intermediates in the preparation of phenylalkylamine calcium channel blockers

DOI: 10.1039/p19960002845

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2845 - 2850 (1996)

Update date:2022-07-29

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Authors:

Gilmore, Jeremy

Prowse, Will

Steggles, David

Urquhart, Michael

Olkowski, Jennifer

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Article abstract of DOI:10.1039/p19960002845

The multigram synthesis of (2S)- and (2R)-2-(1-methylethyl)-5-oxo-2-phenylpentanenitriles 9a and 9b is described, using either (4,R)-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.

Full text of DOI:10.1039/p19960002845

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