Synthesis of hydroxypiperidinecarboxylic acids from pyridinedicarboxylates

Authors
Damsgaard, A Hazell, R Bols, M
Citation
A. Damsgaard et al., Synthesis of hydroxypiperidinecarboxylic acids from pyridinedicarboxylates, ACT CHEM SC, 53(7), 1999, pp. 521-527
Citations number
15
Categorie Soggetti
Chemistry
Journal title
ACTA CHEMICA SCANDINAVICA
ISSN journal
0904213X → ACNP
Volume
53
Issue
7
Year of publication
1999
Pages
521 - 527
Database
ISI
SICI code
0904-213X(199907)53:7<521:SOHAFP>2.0.ZU;2-P
Abstract
(3RS,4SR,5SR)-5-Hydroxy-3-hydroxymethyl-4-piperidinecarboxylic acid 4,3'-la ctone was synthesised in eight steps from ethyl glycinate via selective hyd rolysis and reduction of 4,5-di-(methoxycarbonyl)-3-hydroxypyridine. The re gioisomer (3RS,4RS,5SR)-5-hydroxy-4-hydroxymethyl-3-piperidinecarboxylic ac id 3,4'-lactone was also synthesised. The regio- and stereo-chemistry of th e reactions were confirmed by five X-ray crystallographic structure determi nations.