Preparation of (R)-1-(2-Naphthyl)ethylamine by Enzymatic Kinetic Resolution with A New Acyl Donor

doi:10.6023/cjoc1105101

Chin. J. Org. Chem. ›› 2012, Vol. ›› Issue (03): 526-531.DOI: 10.6023/cjoc1105101 Previous Articles Next Articles

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新型酰基供体用于酶法动力学拆分制备(R)-1-(2-萘基)乙胺的研究

符思敏, 徐刚, 陈永军, 吴坚平, 杨立荣

浙江大学化学工程与生物工程学系杭州 310027

收稿日期:2011-05-10 修回日期:2011-10-20 发布日期:2012-03-24
通讯作者: 徐刚 E-mail:xugang_1030@zju.edu.cn
基金资助:
国家自然科学基金(Nos. 20606030, 20936002)、国家863 计划(No. 2006AA02Z238)以及国家973 计划(Nos. 2011CB710800, 2009CB724706)资助项目.

Preparation of (R)-1-(2-Naphthyl)ethylamine by Enzymatic Kinetic Resolution with A New Acyl Donor

Fu Simin, Xu Gang, Chen Yongjun, Wu Jianping, Yang Lirong

Department of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027

Received:2011-05-10 Revised:2011-10-20 Published:2012-03-24
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 20606030, 20936002), the National High-tech Research and Development Program of China (No. 2011AA02A209) and the Major State Basic Research Development Program of China (Nos. 2011CB710800, 2009CB724706).

Enantiomerically pure (R)-1-(2-naphthyl)ethylamine was firstly prepared by an efficient enzymatic kinetic resolution process. The effects of lipases, solvents, acyl donors, substrate concentration and temperature on the reaction were investigated. It was found that as the acyl donor, 4-chlorophenyl valerate could effectively inhibit the non-selective amidation reaction. The optimal solvent, amine concentration and temperature were toluene, 300 mmol/L and 40 ℃, respectively. Under the optimal conditions mentioned above, an excellent ee_p value (＞99%) at high conversion (50%) in 8 h could be achieved on the kinetic resolution reaction catalyzed by Novozym 435 with the new acyl donor.

Key words: (R)-1-(2-naphthyl) ethylamine, 4-chlorophenyl valerate, Novozym 435, enzymatic kinetic resolution

Cite this article

Fu Simin, Xu Gang, Chen Yongjun, Wu Jianping, Yang Lirong . Preparation of (R)-1-(2-Naphthyl)ethylamine by Enzymatic Kinetic Resolution with A New Acyl Donor[J]. Chin. J. Org. Chem., 2012, (03): 526-531.

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新型酰基供体用于酶法动力学拆分制备(R)-1-(2-萘基)乙胺的研究

Preparation of (R)-1-(2-Naphthyl)ethylamine by Enzymatic Kinetic Resolution with A New Acyl Donor

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