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Syntheses of [4-14c] and [6-14c]nisoldipine

✍ Scribed by D. Scherling; U. Pleiß

Publisher
John Wiley and Sons
Year
1988
Tongue
French
Weight
340 KB
Volume
25
Category
Article
ISSN
0022-2135

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✦ Synopsis

The synthesis of

[ 4-14C]nisoldipine started from dimethyl [ 14C] formamide which was allowed to react with 2-nitrophenyllithium yielding 2-nitro [ 7-14C] benzaldehyde . Knovenagel condensation with isobutyl acetoacetate yielded isobutyl 2-(2-nitr0[7-~~C]benzylidene) acetoacetate. Key reaction step was the cyclizing Michael addition with methyl 3-aminocrotonate to obtain 3-isobutyl 5-methyl 1,4-dihydro-2,6-dimethyl-4-(2-nitro- phenyl) -[ 4-14C]pyridine-3 , 5-dicarboxylate (= [ 4-14C]nisoldipine) . Starting material of the synthesis of [ 6-14C] nisoldipine was barium[ 14C]carbonate which was converted to [ l-14C]acetyl chloride. The acid chloride was condensed with Meldrum's acid (2,2-dimethyl-1,3-dioxane-4,6-dione). The resulting intermediate was treated with boiling methanol to give methyl [3-14C]acetoacetate. Reaction of the 8-ketoester with gaseous ammonia in toluene afforded the corresponding aminocrotonate, which was condensed with isobutyl 2-(2-nitrobenzylidene)-acetoacetate to yield [ 6-14C]nisoldipine.

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Den folgenden Institutionen sind wir fur die Unterstutzung der vorliegenden Arbeit zu grossem Dank verpflichtet : Eke Kloster-Jensen dem Norges Teknisk-Naturvitenskapelige Forskningsrdd in Oslo fur die Gewahrung eines Auslandsstipendiums, E. Kov6ts der Firma Hoffmann-La Roche & Cie. AG. in Basel, A