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Preparation of (R)- and (S)-6-hydroxybuspirone by enzymatic resolution or hydroxylation
- Source :
- Tetrahedron: Asymmetry. 16:2711-2716
- Publication Year :
- 2005
- Publisher :
- Elsevier BV, 2005.
-
Abstract
- 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.
Details
- ISSN :
- 09574166
- Volume :
- 16
- Database :
- OpenAIRE
- Journal :
- Tetrahedron: Asymmetry
- Accession number :
- edsair.doi...........9edda988653835448c5c905474ccf55e