Preparation of (R)- and (S)-6-hydroxybuspirone by enzymatic resolution or hydroxylation

Autor:	Ronald L. Hanson, Ramesh N. Patel, William L. Parker, David B. Brzozowski, Atul S. Kotnis, Mark Liu, Thomas P. Tully
Rok vydání:	2005
Předmět:	chemistry.chemical_classification Stereochemistry Organic Chemistry Catalysis Amino acid Inorganic Chemistry Hydroxylation chemistry.chemical_compound Hydrolysis Enzyme chemistry Yield (chemistry) Acid hydrolysis Physical and Theoretical Chemistry Enantiomer Active metabolite
Zdroj:	Tetrahedron: Asymmetry. 16:2711-2716
ISSN:	0957-4166
DOI:	10.1016/j.tetasy.2005.07.020
Popis:	6-Hydroxybuspirone is an active metabolite of the antianxiety drug buspirone. The (R)- and (S)-enantiomers of 6-hydroxybuspirone were prepared using an enzymatic resolution process. l -Amino acid acylase from Aspergillus melleus (Amano Acylase 30000) was used to hydrolyze racemic 6-acetoxybuspirone to (S)-6-hydroxybuspirone in 95% ee after 45% conversion. The remaining (R)-6-acetoxybuspirone with 88% ee was converted to (R)-6-hydroxybuspirone by acid hydrolysis. The ee of both enantiomers could be improved to 99% by crystallization as a metastable polymorph. (S)-6-Hydroxybuspirone was also obtained in 88% ee and 14.5% yield by hydroxylation of buspirone using Streptomyces antibioticus ATCC 14890.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::9edda988653835448c5c905474ccf55e https://doi.org/10.1016/j.tetasy.2005.07.020 Zobrazit plný text záznamu Full Text from ScienceDirect