2017年1月
PREPARATION OF (R)-3-HYDROXY-N-METHYLPIPERIDINE, A SYNTHETIC KEY INTERMEDIATE OF (R)-MEPENZOLATE, BASED ON THE LIPASE-CATALYZED RESOLUTION OF THE RACEMIC FORM
HETEROCYCLES
- ,
- ,
- ,
- 巻
- 95
- 号
- 1
- 開始ページ
- 370
- 終了ページ
- 379
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.3987/COM-16-S(S)28
- 出版者・発行元
- PERGAMON-ELSEVIER SCIENCE LTD
In this study, a two-step method for the gram-scale synthesis of (R)-3-hydroxy-N-methylpiperidine in 97.8% enantiomeric excess (ee) is reported. The key chiral synthetic intermediate of (R)-mepenzolate was formed in 22% yield over two steps using a commercially available and inexpensive racemic alcohol as the starting material. In the first step, Candida antarctica lipase B-catalyzed kinetic resolution of the racemic alcohol under acetylation conditions was performed to obtain the acetate form of the (R)-enantiomer in 82.1% ee (E 18). The second step involved enantio-enrichment using the same lipase to catalyze deacetylation. The ee of the product (R)-alcohol was further enriched to 97.8%.
- リンク情報
- ID情報
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- DOI : 10.3987/COM-16-S(S)28
- ISSN : 0385-5414
- eISSN : 1881-0942
- Web of Science ID : WOS:000405885400030