Journal of Chemical Research p. 322 - 324 (2014)
Update date:2022-07-29
Topics:
Xue, Feng
Li, Chang-Gong
Zhu, Yong
Lou, Tian-Jun
An improved and efficient process has been developed for a green and scalable preparation of optically pure (1R,2R) - and (1S,2S) -trans-2-aminocyclohexanols. The process utilised hot water to promote the aminolysis of cyclohexene oxide by benzylamine to afford racemic trans-2-(benzylamino)cyclohexanols, which were resolved by sequential and repeated use of (R)- and (S)-mandelic acid. Finally, after treatment of the two salts sequentially with HCl and NaOH and recovery of mandelic acid, liberation was achieved of the optically pure trans-2-benzylaminoaminocyclohexanols which were smoothly debenzylated using a low loading of a Pd/C catalyst to the trans-2-aminocyclohexanols. The synthetic route has been successfully applied to large-scale (1 mol) preparations in good yield.
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