Enzymatic Resolution of cis‐Dimethyl‐1‐acetylpiperidine‐2,3‐dicarboxylate for the Preparation of a Moxifloxacin Building Block
Abstract 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 (2 R ,3 S ) configuration from non‐reacted substrate in...
| Published in: | ChemistrySelect |
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| Main Authors: | , , |
| Format: | Article in Journal/Newspaper |
| Language: | English |
| Published: |
Wiley
2022
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| Subjects: | |
| Online Access: | http://dx.doi.org/10.1002/slct.202104090 https://onlinelibrary.wiley.com/doi/pdf/10.1002/slct.202104090 https://onlinelibrary.wiley.com/doi/full-xml/10.1002/slct.202104090 |
| Summary: | Abstract 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 (2 R ,3 S ) configuration from non‐reacted substrate in the (2 S ,3 R ) 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 (2 R ,3 S ) configuration can be used for the preparation of a neuromediator analogue. The lipase demonstrated enantioselectivity towards the (2 R ,3 S ) 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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