Articles

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

Received date: 2011-05-10

  Revised date: 2011-10-20

  Online 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).

Abstract

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 eep 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.

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]. Chinese Journal of Organic Chemistry, 2012 , (03) : 526 -531 . DOI: 10.6023/cjoc1105101

References

[1] Ghosh, A. K.; Takayama, J.; Aubin, Y.; Ratia, K.; Chaudhuri, R.;Baez, Y.; Sleeman, K.; Coughlin, M.; Nichols, D. B.; Mulhearn, D.C.; Prabhakar, B. S.; Baker, S. C.; Johnson, M. E.; Mesecar, A. D.J. Med. Chem. 2009, 52, 5228.  

[2] Fredga, A.; Sjoberg, B.; Sandberg, R. Acta Chem. Scand. 1957, 11,1609.  

[3] Mereyala, H. B.; Pola, P. Tetrahedron: Asymmetry 2003, 14, 2683.  

[4] Shimada, T.; Kobayashi, Y.; Saigo, K. Tetrahedron: Asymmetry2005, 16, 3807.  

[5] Hu, J.; Dong, J.; Shi, X.-X. Chin. J. Synth. Chem. 2010, (1), 61 (inChinese).(胡健, 董菁, 施小新, 合成化学, 2010, (1), 61.)

[6] Szatmári, I.; Sillanp??, R.; Fül?p, F. Tetrahedron: Asymmetry 2008,19, 612.  

[7] Gül, N.; Nelson, J. H. J. Mol. Struct. 1999, 475, 121.  

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

[9] Mereyala, H. B.; Pola, P. Tetrahedron: Asymmetry 2003, 14, 2683.  

[10] Kazuhiko, S.; Yuka, K.; Takanobu. [10] Kazuhiko, S.; Yuka, K.;Takanobu. JP 2005060231, 2005 [Chem. Abstr. 2005, 142,297888].

[11] Guijarro, D.; Pablo, ó.; Yus, M. J. Org. Chem. 2010, 75, 5265.  

[12] Kadyrov, R.; Thomas, H. R. Angew. Chem., Int. Ed. 2003, 42,5472.  

[13] Savile, C. K.; Janey, J. M.; Mundorff, E. C.; Moore, J. C.; Tam, S.;Jarvis, W. R.; Colbeck, J. C.; Krebber, A.; Fleitz, F. J.; Brands, J.;Devine, P. N.; Huisman, G. W.; Hughes, G. J. Science 2010, 329,305.  

[14] Shen, H.-Y.; Tian, G.-L.; Ye, Y.-H. Chin. J. Org. Chem. 2003, 23,221 (in Chinese).(沈鸿雁, 田桂玲, 叶蕴华, 有机化学, 2003, 23, 221.)

[15] Huang, L.-Q.; Chen, D.-W.; Yang, H. Chin. J. Org. Chem. 2005,25, 1575 (in Chinese).(黄丽琴, 陈道文, 杨红, 有机化学, 2005, 25, 1575.)

[16] Jin, Y.; Wu, J.-P.; Xu, G.; Yang, L.-R. Chin. J. Org. Chem. 2006,26, 1384 (in Chinese).(金勇, 吴坚平, 徐刚, 杨立荣, 有机化学, 2006, 26, 1384.)

[17] Xu, G.; Cheng, Y.-M.; Wu, J.-P.; Yang, L.-R. Chin. J. Org. Chem.2007, 27, 857 (in Chinese).(徐刚, 程永梅, 吴坚平, 杨立荣, 有机化学, 2007, 27, 857.)

[18] Wang, M.-H.; Yang, G.; Yang, L.-R. Chin. J. Org. Chem. 2008, 28,1398 (in Chinese).(王明慧, 杨光, 杨立荣, 有机化学, 2008, 28, 1398.)

[19] Wang, S.-Z.; Wu, J.-P.; Xu, G.; Yang, L.-R. Chin. J. Org. Chem.2008, 9, 1584 (in Chinese).(王世珍, 吴坚平, 徐刚, 杨立荣, 有机化学, 2008, 9, 1584.)

[20] Youshko, M. I.; Rantwijk, F. V.; Sheldon, R. A. Tetrahedron:Asymmetry 2001, 12, 3267.  

[21] Davis, B. A.; Durden, D. A. Synth. Commun. 2001, 31, 569-578.

[22] Yang, B.; Taeko, I.; Zhang, S.-S. Chem. J. Chin. Univ. 2001, 22,1332 (in Chinese).(杨波, 泉多惠子, 张书圣, 高等学校化学学报, 2001, 22, 1332.)

[23] Xu, G.; Dai, J.-Q.; Wu, J.-P.; Yang, L.-R. J. Chem. Ind. Eng. 2007,58, 1741 (in Chinese). (徐刚, 戴军强, 吴坚平, 杨立荣, 化工学报, 2007, 58, 1741.)

[24] Alexander, E. R.; Misegades, A. L. J. Am. Chem. Soc. 1948, 70,1315.  

[25] Malanga, C.; Urso, A.; Lardicci, L. Tetrahedron Lett. 1995, 36,8859.  
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