Nonanoic acid, reduction

On an industrial scale, the traditional method for cleavage of carbon-carbon double bonds is ozonolysis, used for the manufacture of azelaic acid and nonanoic acids from oleic acid, and of butane tetracarboxylic acid from tetrahydrophthalic anhydride. The process is effectively a quantitative and mild process.178 However, it is capital and energy intensive. The intermediate ozonide is worked up either reductively or oxidatively to produce the aldehyde, ketone or carboxylic acid. Hydrogen peroxide is the common oxidizing agent used in the second step.179-181 Oxygen can also be used either alone182 or in combination with zeolites.183 Reviews on ozonolysis are available and the reader is directed to reference 184 for further information. 

With respect to polymer synthesis and to the development of biologically active compounds in recent years, the ozonolysis/reductive cleavage of OA or MO or the fragmentation of the intermediary carbonyl oxide to 9-oxononanoic acid and its respective methyl ester gained attention again [33-39]. 9-Oxononanoic acid can be easily converted to 9-amino- or 9-hydroxynonanoic acid as sources for polyamides and polyesters [40]. A French patent claimed the synthesis of oxo-nonanoic acid via homometathesis of OA, followed by reductive ozonolysis of the unsaturated C18 diacid obtained [41]. 

Only one example was found where this class of amino acids was produced. Oxidation of 7.246 gave a ketone and treatment with boron trifluoride led to the conjugated ketone, 7.247.132 Conjugate addition of azide, reduction to the amine and cyclization gave diastereomeric methyl 9-(3-hexyl-2-aziridino)nonanoic acid (J.248 and 7.249). The final step in that sequence proceeded in only 37% yield. If the alkenyl moiety was converted to an epoxide moiety, aziridine carboxylic acids were prepared in good yield, via the azide.132... 

As seen in previous examples, the intermediate iminium salt produced by reductive amination need not be isolated, and reduction in situ is very common.52 A mixture of sodium cyanoborohydiide and ammonium acetate was used for the reductive amination of the aldehyde derived from acid hydrolysis of the dioxolane moiety in 1,94. In this example, the dioxolane moiety was hydrolyzed to release the aldehyde, which reacted with NaBH3CN/NH40Ac to produce an amine. The amine was then protected as its benzenesulfonate. The final product was methyl 9-amino-nonanoate benzenesulfonamide, 1.95 (20% overall yield).53... 

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