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Synthesis and resolution of substituted pipecolic acids

โœ Scribed by C.G. Overberger; M.D. Shalati

Publisher
Elsevier Science
Year
1983
Tongue
English
Weight
806 KB
Volume
19
Category
Article
ISSN
0014-3057

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โœฆ Synopsis

A new general method for the preparation of 2-alkyl-pipecolic acids has been developed. The syntheses of 2-methyl-, 2-benzyl-and cis-6-methylpipecolic acids are described. (-)S-and (+)R-2-methylpipecolic acids were resolved by fractional crystallization of the quinine salt of their N-carbobenzoxy derivative. Isolation of (-)S-cis-6-methylpipecolic acid required the use of 4-phenylbenzyloxycarbonyl as protecting group to achieve selective crystallization of the quinine salt. The absolute configurations of these compounds were determined by circular dichroism.

๐Ÿ“œ SIMILAR VOLUMES

A facile synthesis of 3-substituted pipe
A facile synthesis of 3-substituted pipecolic acids, chimeric amino acids
โœ Gergely M. Makara; Garland R. Marshall ๐Ÿ“‚ Article ๐Ÿ“… 1997 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 247 KB

Three protected 3-substituted pipecolic acid analogs were prepared as constrained chimeric amino acid building blocks. The concise synthetic route enables the synthesis of other derivatives with sidechaln functionality of amino acids as well.