3-Nitrobenzaldehyde → 2,6-Dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(3-[4-(2-tetrahydropyran-2-yloxyethyl)phenoxy]propoxycarbonyl)-1,4-dihydropyridine

Participants

Reaction Steps

An ω-phenylalkylacetoacetate derivative (2) is reacted with an alkyl β-aminoalkenoate (3) (for example, methyl β-aminocrotonate) and a benzaldehyde derivative of formula 4 under Hantzsch dihydropyridine synthesis conditions (see, e.g., Fox, et al., J. Org. Chem., 16, 1259 (1951)) to form a 4-phenyl-2,6-dialkyl-1,4-dihydropyridine dicarboxylate diester derivative (1). For example, 3-(4-[2-(tetrahydropyran-2-yloxy)ethyl]phenoxy)propyl acetoacetate (2) is reacted with methyl β-aminocrotonate and 3-nitrobenzaldehyde to produce 2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(3-[4-(2-tetrahydropyran-2-yloxyethyl)phenoxy]propoxycarbonyl)-1,4-dihydropyridine (1). (Scheme I)

Provenance & Evidence