Preparation of (R)-1-Aminoindan by Dynamic Kinetic Resolution

doi:10.6023/cjoc201311048

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (5): 933-937.DOI: 10.6023/cjoc201311048 Previous Articles Next Articles

动态动力学拆分制备（R）-1-氨基茚满

戴晓庭, 吴坚平, 孟枭, 徐刚, 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:2013-11-30 修回日期:2013-12-30 发布日期:2014-01-24
通讯作者: 徐刚 E-mail:xugang_1030@zju.edu.cn
基金资助:
国家重点基础研究发展计划（No. 2011CB710800）、国家高技术研究发展计划（No. 2011AA02A209）、国家自然科学基金（No. 20936002）资助项目.

Preparation of (R)-1-Aminoindan by Dynamic Kinetic Resolution

Dai Xiaoting, Wu Jianping, Meng Xiao, Xu Gang, Yang Lirong

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

Received:2013-11-30 Revised:2013-12-30 Published:2014-01-24
Supported by:
Project supported by the National Basic Research Program of China (No. 2011CB710800), the Hi-Tech Research and Development Program of China (No. 2011AA02A209), the National Natural Science Foundation of China (No. 20936002).

Enantiomerically pure (R)-1-aminoindan was firstly prepared by dynamic kinetic resolution. A novel racemization catalyst Pd/layered double-hydroxide-dodecyl sulfate anion (PD/LDH-DS) was prepared and used in the racemization of (S)-1-aminoindan, and the reaction condition was investigated. It was found that the catalyst had superior racemization ability. On this basis, combined with reaction condition of lipase Novozym 435, it was confirmed that toluene was the reaction solvent, 4-chlorophenyl valerate was the acyl donor, concentration of substrate was 82.5 mmol/L, reaction temperature was 55 ℃, and the reaction time was 15 h. Under the condition, (R)-1-aminoindan valerate was prepared with excellent ee_P value (>99%) and high conversion (>99%).

Key words: dynamic kinetic resolution, (R)-1-aminoindan, racemization catalyst, Novozym 435

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Dai Xiaoting, Wu Jianping, Meng Xiao, Xu Gang, Yang Lirong. Preparation of (R)-1-Aminoindan by Dynamic Kinetic Resolution[J]. Chin. J. Org. Chem., 2014, 34(5): 933-937.

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[1] Youdim, M. B. H.; Finberg, J. P. M.; Levy, R.; Sterling, J.; Lerner, D.; Berger-Paskin, T.; Yellin, H. US 5457133, 1995 [Chem. Abstr. 1998, 128, 312931].

[2] Youdim, M. B. H.; Finberg, J. P. M.; Levy, R.; Sterling, J.; Lerner, D.; Berger-Paskin, T.; Yellin, H.; Veinberg, A. US 5532415, 1996 [Chme. Abstr. 1998, 128, 312931].

[3] Brewster, J. H.; Buta, J. G. J. Am. Chem. Soc. 1966, 88, 2233.

[4] Brewster, J. H.; Buta, J. G. J. Am. Chem. Soc. 1966, 88, 2233.

[5] Zhao, J.; Wang, Y.-D.; Yang, S.-Y.; Jin, D.-S.; Wei, X.-H. Chin. J. Org. Chem. 1997, 17, 87 (in Chinese).

(赵军, 王亚东, 杨世琰, 金道森, 魏学红, 有机化学, 1997, 17, 87.)

[6] Liu, X.-L.; Liu, Y.-H.; Shi, Y.-C.; Jian, P.-M. Chin. J. Org. Chem. 2002, 22, 482 (in Chinese).

(刘晓岚, 刘永红, 石尧成, 菅盘名, 有机化学, 2002, 22, 482.)

[7] Gao, Y.-L.; Yang, L.-H.; Song, S.-J.; Ma, J.-J.; Tang, R.-X,; Bian, R.-H.; Liu, H.-Y.; Wu, Q.-H.; Wang, C. Chin. J. Org. Chem. 2008, 28, 8 (in Chinese).

(高勇军, 杨丽华, 宋双居, 马晶军, 唐然肖, 边瑞环, 刘海燕, 吴秋华, 王春, 有机化学, 2008, 28, 8.)

[8] Shin, J. S.; Kim, B. G.; Shin, D. H. Enzyme Microb. Technol. 2001, 29, 232.

[9] Shin, J. S.; Kim, B. G.; Liese, A.; Wandrey, C. Biotechnol. Bioeng. 2001, 73, 179.

[10] Gül, N.; Nwlaon, J. H. J. Mol. Struct. 1999, 475, 121.

[11] Pallavicini, M.; Bolchi, C.; Fumagalli, L.; Valoti, E.; Villa, L. Tetrahedron: Asymmetry 2002, 13, 2277.

[12] Szatmári, I.; Sillanpää, R.; Fülöp, F. Tetrahedron: Asymmetry 2008, 19, 612.

[13] Reddy, V. G.; Khanna, N.; Singh, N. Biochem. Biophys. Res. Commun. 2001, 282, 409.

[14] Reetz, M. T.; Schimossek, K. Chimia 1996, 50, 668.

[15] Parvulescu, A. N.; Jacobs, P. A.; De Vos, D. E. Chem. Eur. J. 2007, 13, 2034.

[16] Shakeri, M.; Tai, C. W.; Gothelid, E.; Oscarsson, S.; Backcall, J. E. Chem. Eur. J. 2011, 17, 13269.

[17] Paetzold, J.; Bäckvall, J. E. J. Am. Chem. Soc. 2005, 127, 17620.

[18] Kim, M. J.; Kim, W. H.; Han, K.; Choi, Y. K.; Park, J. Org. Lett. 2007, 9, 1157.

[19] Andrade, L. H.; Silva, A. V.; Pedrozo, E. C. Tetrahedron Lett. 2009, 50, 4331.

[20] Shi, J.; Li, X.; Wang, Q. R.; Zhang, Y. H.; Tang, Y. J. Catal. 2012, 291, 87.

[21] Xu, G.; Dai, X.; Fu, S.; Wu, J.; Yang, L. Tetrahedron Lett. 2014, 55, 397.

[22] Liu, S.-Y.; Zhou, Q.-Z.; Jin, Z.-N.; Jiang, H.-J.; Jiang, X.-Z. Chin. J. Catal. 2010, 31, 557 (in Chinese).

(刘诗咏, 周其忠, 金正能, 蒋华江, 姜玄珍, 催化学报, 2010, 31, 557.)

动态动力学拆分制备（R）-1-氨基茚满

Preparation of (R)-1-Aminoindan by Dynamic Kinetic Resolution

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