Reduction of ethyl benzoylacetate and selective pvotection of 2-(3-hydroxy-l-phenylpropyl)-4-methylphenol: A new and facile synthesis of tolterodine
- Title
- Reduction of ethyl benzoylacetate and selective pvotection of 2-(3-hydroxy-l-phenylpropyl)-4-methylphenol: A new and facile synthesis of tolterodine
- Author
- 이학준
- Issue Date
- 2007-09
- Publisher
- American Chemical Society
- Citation
- Organic Process Research and Development, v. 11, NO. 5, Page. 918-921
- Abstract
- A new and facile synthesis of tolterodine using ethyl benzoylacetate as the starting material was developed. Reduction using sodium borohydride in methanol followed by Friedel-Crafts alkylation utilizing FeCl3 center dot 6H(2)O as catalyst lead to the known 2-(3-hydroxy1-phenylpropyl)-4-methylphenol intermediate. Consecutive protection of phenolic OH with p-toluenesulfonyl chloride via two-phase reaction and conversion of aliphatic OH using p-nitrobenzenesulfonyl chloride facilitates direct substitution of diisopropylamine. After simultaneous deprotection of the tosyl group, optically pure (R)-tolterodine center dot L-tartrate was obtained by resolution using L-tartaric acid with 99.99% purity.
- URI
- https://pubs.acs.org/doi/10.1021/op7001134https://repository.hanyang.ac.kr/handle/20.500.11754/183994
- ISSN
- 1083-6160;1520-586X
- DOI
- 10.1021/op7001134
- Appears in Collections:
- COLLEGE OF SCIENCE AND CONVERGENCE TECHNOLOGY[E](과학기술융합대학) > CHEMICAL AND MOLECULAR ENGINEERING(화학분자공학과) > Articles
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