A facile synthesis of enantiomerically pure 1-(piperazin-2-yl)ethan-1-ol derivatives from (2S,3R)-threonine

Authors
Soukara, S Wunsch, B
Citation
S. Soukara et B. Wunsch, A facile synthesis of enantiomerically pure 1-(piperazin-2-yl)ethan-1-ol derivatives from (2S,3R)-threonine, SYNTHESIS-S, (10), 1999, pp. 1739-1746
Citations number
13
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881 → ACNP
Issue
10
Year of publication
1999
Pages
1739 - 1746
Database
ISI
SICI code
0039-7881(199910):10<1739:AFSOEP>2.0.ZU;2-B
Abstract
Starting from the proteinogenic amino acid (2S,3R)-threonine (4) a novel me thod for the preparation of enantiomerically pure 1-(1-benzylpiperazin-2-yl )ethan-1-ols with various substituents in position 4 (15 - 20) is described . The sequence involves as key step the LiAlH4, reduction of the bicyclic p iperazinediones 11a,b-14a,b, which establishes the l-benzyl protective grou p and simultaneously liberates the l-hydroxyethyl side chain for further tr ansformations.