Synthesis and X-ray crystal structure of 1,4-dihydro-2,6-dimethyl-4-(2′-isopropylphenyl)- 3,5-pyridine-dicarboxylic acid dimethyl ester: A nifedipine analogue

✍ Scribed by Robert B. Palmer; Niels H. Andersen

• Publisher: Elsevier Science
• Year: 1996
• Tongue: English
• Weight: 242 KB
• Volume: 6
• Category: Article
• ISSN: 0960-894X
• DOI: 10.1016/0960-894x(96)00396-4

✦ Synopsis

We report the synthesis and X-ray crystal structure of 1,4-dihydro-2,6-dimethyl-4-(2'isopropylphenyl)-3,5-pyridine-dicarboxylic acid dimethyl ester (4), an analogue of the 1,4dihydropyridine calcium channel antagonist, nifedipine. Solution state NOE data indicate the presence of both rotameric forms. The solid state shows exclusively one rotamer of 4 (that in which the 2'-isopropyl substituent is syn with C4H, which is also the major solution state rotamer). The 3,5-methyl esters adopt an ap/sp orientation with respect to the dihydropyridine double bonds in the solid state.