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Diastereoselective esterification of (±)-N-trifluoroacetyl pipecolic acid using (S)-α-methyl pantolactone: synthesis of (S)-N-Boc pipecolic acid and (S)-N-Boc-2-piperidinemethanol

✍ Scribed by Monique Calmès; Françoise Escale; Marc Rolland; Jean Martinez

Publisher
Elsevier Science
Year
2003
Tongue
English
Weight
168 KB
Volume
14
Category
Article
ISSN
0957-4166

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✦ Synopsis

Racemic N-trifluoroacetyl pipecolic acid has been converted into (S)-N-Boc-pipecolic acid or (S)-N-Boc-2-piperidinemethanol by DCC/DMAP-induced diastereoselective esterification with (S)-a-methyl pantolactone, followed by a saponification or a reduction reaction and N-Boc protection.

📜 SIMILAR VOLUMES

A regioselective reductive cleavage of b
A regioselective reductive cleavage of benzylidene acetal: stereoselective synthesis of N-Boc-protected cis-(2R,3S)-3-hydroxy pipecolic acid
✍ Ponminor Senthil Kumar; Sundarababu Baskaran 📂 Article 📅 2009 🏛 Elsevier Science 🌐 French ⚖ 341 KB

A stereoselective synthesis of N-Boc-protected cis-(2R,3S)-3-hydroxy pipecolic acid, starting from D-glucose is described. The key step in the overall synthesis is a highly regioselective reductive cleavage of benzylidene acetal 13 leading to hydroxymethyl piperidine derivative 14.