chemia - Studia

SYNTHESIS AND LIPASE CATALYSED KINETIC RESOLUTION OF RACEMIC AMINES
(R)-N-(Heptan-2-yl)acetamide (R)-3a: yellow oil; 1 H NMR (300 MHz, DMSO-d 6 ,
δ ppm): 0.85 (3H, t, J=7.0 Hz, CH 3 ); 0.99 (3H, d, J=6.6 Hz, CH 3 ); 1.15-1.40 (8H, m,
4×CH 2 ); 1.76 (3H, s, CH 3 ); 3.70 (1H, m, CHN); 7.62 (1H, br d, J=8.1 Hz, NH); 13 C NMR
(75 MHz, DMSO-d 6 , δ ppm): 14.38 (CH 3 ); 21.22 (CH 3 ); 22.52 (CH 2 ); 23.14 (CH 3 );
25.86 (CH 2 ); 31.72 (CH 2 ); 36.57 (CH 2 ); 44.54 (CH); 168.76 (CO); IR (cm -1 ): 3275,
3079, 2959, 2928, 2858, 1638, 1550, 1453, 1371, 1293, 1157, 974, 726, 608
(R)-N-(4-Phenylbutan-2-yl)acetamide (R)-3b: pale yellow liquid; 1 H NMR
(300 MHz, DMSO-d 6 ): 1.04 (3H, d, J=6.6 Hz, CH 3 ); 1.57-1.71 (2H, m, CH 2 ); 1.81
(3H, s, CH 3 ); 2.48-2.61 (2H, m, CH 2 ); 3.75 (1H, m, CHN); 7.11-7.21 (3H, m, 3×CH);
7.22-7.31 (2H, m, 2×CH); 7.74 (1H, br d, J=8.1 Hz, NH); 13 C NMR (75 MHz, DMSO-d 6 ):
21.24 (CH 3 ); 23.24 (CH 3 ); 32.42 (CH 2 ); 38.44 (CH 2 ); 44.42 (CH); 126.09 (CH); 128.83
(4×CH); 142.36 (C); 168.93 (CO); IR (cm -1 ): 3271, 3084, 3065, 2967, 2929, 1637, 1546,
1495, 1453, 1371, 1292, 1144, 967, 746, 698, 609
(R)-N-(1-Phenylethyl)acetamide (R)-3c: tawny crystals; 1 H NMR (300 MHz,
DMSO-d 6 ): 1.33 (3H, d, J=7.2 Hz, CH 3 ); 1.84 (3H, s, CH 3 ); 4.90 (1H, m, CHN); 7.14-7.26
(1H, m, CH); 7.27-7.36 (4H, m, 4×CH); 8.30 (1H, br d, J=7.9 Hz, NH); 13 C NMR (75 MHz,
DMSO-d 6 ): 22.47 (CH 3 ); 22.64 (CH 3 ); 47.78 (CH); 125.93 (2×CH); 126.64 (CH);
128.28 (2×CH); 144.87 (C); 168.30 (CO); IR (cm -1 ): 3266, 3071, 3023, 2980, 2929, 1643,
1555, 1451, 1375, 1286, 1278, 1216, 1136, 1070, 1027, 763, 702, 620, 533, 501
(R)-N-(1,2,3,4-Tetrahydronaphthalen-1-yl)acetamide (R)-3d: brown crystals;
1 H NMR (300 MHz, DMSO-d 6 ): 1.58-1.78 (2H, m, CH 2 ); 1.79-1.95 (5H, m, CH 3 +CH 2 );
2.63-2.82 (2H, m, CH 2 ); 4.90-5.03 (1H, m, CHN); 7.04-7.20 (4H, m, 4×CH); 8.22
(1H, br d, J=8.5 Hz, NH); 13 C NMR (75 MHz, DMSO-d 6 ): 20.47 (CH 2 ); 23.20 (CH 3 );
29.25 (CH 2 ); 30.48 (CH 2 ); 46.86 (CH); 126.28 (CH); 127.22 (CH); 128.67 (CH); 129.28
(CH); 137.45 (C); 138.07 (C); 169.05 (CO); IR (cm -1 ; KBr): 3240, 3062, 2928, 2854,
1633, 1544, 1445, 1371, 1283, 1095, 1038, 965, 764, 739, 610, 536, 446
ACKNOWLEDGEMENTS
This research work was supported by the Hungarian National Office for
Research and Technology (NKFP-07-A2 FLOWREAC). This work is also related to
the scientific program of "Development of quality-oriented and harmonized R+D+I
strategy and functional model at BME" project (TÁMOP-4.2.1/B-09/1/KMR-2010-0002),
supported by the New Hungary Development Plan. The authors thank Dr. György
Szakács (Budapest University of Technology and Economics, Hungary) and Dr. Balázs
Erdélyi (Fermentia Ltd, Budapest, Hungary) for the BUTE 3 lipase preparations.
REFERENCES
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2. T.A. Unger, Ed., „Pesticide Synthesis Handbook” Noyes Publications, Park Ridge,
1996.
3. W. Herbst, K. Hunger, Eds., „Industrial Organic Pigments: Production, Properties,
Applications (3rd Completely Revised Edition)” Wiley-VCH, Weinheim, 2004.
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