Enzymatic Resolution of cis-Dimethyl-1-acetylpiperidine-2,3-dicarboxylate for the Preparation of a Moxifloxacin Building Block
This work presents the enantioselective resolution of a water-soluble racemic mixture of cis-dimethyl 1-acetylpiperidine-2,3-dicarboxylate catalyzed by Candida antarctica lipase B. The separation of the carboxylic acid product in its (2R,3S) configuration from non-reacted substrate in the (2S,3R) co...
| Published in: | ChemistrySelect |
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| Main Authors: | , , |
| Other Authors: | , , |
| Format: | Article in Journal/Newspaper |
| Language: | English |
| Published: |
John Wiley and Sons Inc
2022
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| Subjects: | |
| Online Access: | http://hdl.handle.net/11577/3444199 https://doi.org/10.1002/slct.202104090 |
| Summary: | This work presents the enantioselective resolution of a water-soluble racemic mixture of cis-dimethyl 1-acetylpiperidine-2,3-dicarboxylate catalyzed by Candida antarctica lipase B. The separation of the carboxylic acid product in its (2R,3S) configuration from non-reacted substrate in the (2S,3R) configuration was easily obtained by organic phase extraction. The latter molecule can be used as an enantiomerically pure precursor in the synthesis of (4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridine, an expensive building block in the production of the antibiotic Moxifloxacin. On the other hand, the hydrolyzed product in the (2R,3S) configuration can be used for the preparation of a neuromediator analogue. The lipase demonstrated enantioselectivity towards the (2R,3S) substrate enantiomer and regioselectivity towards the ester in position 3 of the molecule. Studies of hydrolysis kinetics and the use of the immobilized enzyme were performed to evaluate its industrial application. |
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