186763-23-5Relevant academic research and scientific papers
Novel N-substituted alpha aminoacid amides as calcium channel modulators
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, (2008/06/13)
The compounds of formula I and derivatives thereof have been found to be active in tests that show modulation of voltage-dependent calcium channels, and are thus indicated for use in the treatment of diseases in which such modulation is beneficial, in par
Convenient synthesis of (2R)- and (2S)-2-(1-methylethyl)-5-oxo-2-phenylpentanenitrile, intermediates in the preparation of phenylalkylamine calcium channel blockers
Gilmore, Jeremy,Prowse, Will,Steggles, David,Urquhart, Michael,Olkowski, Jennifer
, p. 2845 - 2850 (2007/10/03)
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.
