Facile, alternative route to Lubeluzole, its enantiomer, and the racemate

Lubeluzole [(S)‐9] has been synthesized by a convergent synthesis, alkylation of N‐methyl‐N‐piperidin‐4‐yl‐1,3‐benzothiazol‐2‐amine (4) with (+)‐(R)‐1‐chloro‐3‐(3,4‐difluorophenoxy)propan‐2‐ol [(+)‐(R)‐8] being the key step. Alcohol (+)‐(R)‐8 was obtained from commercially available (R)‐epichlorohyd...

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Bibliographic Details
Published in:Chirality (New York, N.Y.) N.Y.), 2006, Vol.18 (4), p.227-231
Main Authors: Bruno, Claudio, Carocci, Alessia, Catalano, Alessia, Cavalluzzi, Maria M., Corbo, Filomena, Franchini, Carlo, Lentini, Giovanni, Tortorella, Vincenzo
Format: Article
Language:English
Subjects:
Cardiovascular Agents - chemical synthesis
Cardiovascular Agents - chemistry
enantiomeric excess
enantiomers
Molecular Structure
Piperidines - chemical synthesis
Piperidines - chemistry
sodium channel
Stereoisomerism
stereospecific synthesis
stroke
Thiazoles - chemical synthesis
Thiazoles - chemistry
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Summary:Lubeluzole [(S)‐9] has been synthesized by a convergent synthesis, alkylation of N‐methyl‐N‐piperidin‐4‐yl‐1,3‐benzothiazol‐2‐amine (4) with (+)‐(R)‐1‐chloro‐3‐(3,4‐difluorophenoxy)propan‐2‐ol [(+)‐(R)‐8] being the key step. Alcohol (+)‐(R)‐8 was obtained from commercially available (R)‐epichlorohydrin [(R)‐6], while the thiazole derivative 4 was easily obtained starting from N‐protected piperidin‐4‐one (1) in a three‐step procedure. The same method was used in order to obtain both the (R)‐stereoisomer of lubeluzole [(R)‐9] and its racemate [(RS)‐9]. Overall yields ranged from 20% to 35%. The enantiomeric excess values for (S)‐9 and (R)‐9 were 97% and 94% respectively, as analyzed by chiral HPLC. Chirality, 2006. © 2006 Wiley‐Liss, Inc.
ISSN:0899-0042
1520-636X
DOI:10.1002/chir.20240