Aza-Belluš-Claisen rearrangement-enabled synthesis of racemic tapentadol and its stereoisomers

Chinese Journal of Chemistry

Volumn 31, Issue 3, 2013, Pages 317-n/a

  Bai, Donghu ^a,c   Huang, Sha Hua ^a,b   Lin, Zuming ^a   Yang, Lin ^a   Dai, Junzeng ^a,b   Huang, Meng Yuan ^a,c   Jia, Xueshun ^c   Hong, Ran ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b SHANGHAI INSTITUTE OF TECHNOLOGY   (China)

^c SHANGHAI UNIVERSITY   (China)

Author keywords

Bellu Claisen rearrangement; hydrogenation; stereoselective; Tapentadol; zwitterion

Indexed keywords

EID: 84875133828     PISSN: 1001604X     EISSN: 16147065     Source Type: Journal    
DOI: 10.1002/cjoc.201300081     Document Type: Article

References (36)

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23. Other asymmetric syntheses of Tapentadol are also reported, see:, Sun, Z.-K.,;, Liu, Y.-J.,;, Li, H.-H.,;, Wang, M.-J.,;, Zhang, N.-Y.,;, Wang, Z.-S., WO 2011026314 A1 Chem. Abstr., 2010, 154, 310327.
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34. The detailed mechanistic study on aza-Belluš-Claisen rearrangement remains largely unexplored and awaits further in-depth investigation. For discussion on the mechanism of Claisen rearrangement, see: (a) Rehbein, J.,;, Hiersemann, M., In The Claisen Rearrangement, Eds.:, Hiersemann, M.,;, Nubbemeyer, U., Wiley-VCH, 2007, 11, p. 525.
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36. An Ireland-Claisen rearrangement was first disclosed in the synthesis of Tapentadol, see: Vlaskova, R.; Hajicek, J.; Zezula, J., WO 2012089181 A1, 2012. In this patent, anti-isomer was obtained in excellent stereochemistry control from the E-allylic alcohol. However, the detailed reaction conditions were not disclosed for the generation of E-enolate, which was clearly required if the desired [3, 3]-sigmatropic rearrangement crosses over the chair-like transition state. After chemically resolving the corresponding acid, an extra step to install dimethylamine was necessary in the patent synthesis. The spectra data of anti-3 and synthetic, rac-Tapentadol in our synthesis are identical with the reported data in ref. [15] and ref. [12], respectively.