An improved and efficient process for the scalable preparation of optically pure trans-2-aminocyclohexanols

作者：Xue Feng^*; Li Chang Gong; Zhu Yong; Lou Tian Jun

来源：Journal of Chemical Research, 2014, 38(5): 322-324.

DOI：10.3184/174751914X13977299691549

• trans-2-(benzylamino) cyclohexanol
• chiral resolution
• enantiopure (1R, 2R)-trans-2-aminocyclohexanol
• enantiopure (1S, 2S)-trans-2-aminocyclohexanol

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.

• 出版日期2014-5
• 单位河南科技学院