Preparation of ( R)- and ( S)-6-hydroxybuspirone by enzymatic resolution or hydroxylation
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...
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Published in | Tetrahedron: asymmetry Vol. 16; no. 16; pp. 2711 - 2716 |
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Main Authors | , , , , , , |
Format | Journal Article |
Language | English |
Published |
Elsevier Ltd
22.08.2005
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Online Access | Get full text |
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Summary: | 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. |
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ISSN: | 0957-4166 1362-511X |
DOI: | 10.1016/j.tetasy.2005.07.020 |