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Aza‐Belluš‐Claisen Rearrangement‐Enabled Synthesis of Racemic Tapentadol and Its Stereoisomers
Author(s) -
Bai Donghu,
Huang ShaHua,
Lin Zuming,
Yang Lin,
Dai Junzeng,
Huang MengYuan,
Jia Xueshun,
Hong Ran
Publication year - 2013
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201300081
Subject(s) - chemistry , tapentadol , stereocenter , amide , alkene , stereochemistry , vicinal , claisen rearrangement , ketene , molecule , combinatorial chemistry , enantioselective synthesis , organic chemistry , opioid , biochemistry , receptor , catalysis
A concise synthesis of racemic Tapentadol and its stereoisomers was presented. The key step was a TiCl 4 ·THF 2 ‐catalzyed aza‐Belluš‐Claisen rearrangement to create two vicinal tertiary carbon stereogenic centers. The subsequent reduction of amide and hydrogenation of alkene delivered Tapentadol and its stereoisomers. The current approach offers a practical synthetic route to access this class of pharmaceutically significant molecules.
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