Sessiline
[5-(5-oxo-pyrrolidin-2-yloxymethyl)-furan-2-carbaldehyde
5-(5-oxo-pyrrolidin-2-yloxymethyl)-furan-2-carbaldehyde
Scheme 4. The synthesis of sessiline (1).
Sessiline (1)
200 mg (1.98 mmol) 5-hydroxypyrrolidin-2-one (2) and 800 mg (6.34 mmol) 5‑hydroxymethylfurfural (3) were stirred at 60˚C under neat conditions for 1 hour. Then the reaction mixture was diluted with 1 - 2 ml dichloro- methane, filtered, the solid washed with 3 × 2 ml dichloromethane, and air-dried with suction. 225 mg (54%) pure 1 was obtained as colourless crystals. Rf 0.47 (acetone:hexane = 2:1).
Mp.: 169˚C - 172˚C (lit.: 171˚C - 172˚C [1] ).
IR νmax(KBr, cm−1): 3321, 3176, 3117, 2965, 2896, 2863, 2790, 2763, 1772, 1709, 1666, 1531, 1463, 1412, 1389, 1338, 1284, 1276, 1262, 1250, 1208, 1201, 1177, 1096, 1062, 1030, 1007.
1H NMR (400 MHz, DMSO-d6)
δH 1.86 - 1.95 (m, 1H, Hx-4’);
2.01 - 2.10 (m, 1H, Hx-3’);
2.16 - 2.34 (m, 2H, Hy-4’, Hy-3’);
4.49 + 4.58 (AB, 2 × 1H, Jgem = 13.2 Hz, CHO);
5.02 (m, 1H, H-5’);
6.73 (d, 1H, J = 3.4 Hz, H-4);
7.51 (d, 1H, J = 3.4 Hz, H-3);
8.80 (s, 1H, NH);
9.58 (s, 1H, CH=O).
13C NMR (100 MHz, DMSO-d6)
δC 27.5 (C-4’);
27.9 (C-3’);
60.3 (CH2O);
85.2 (C-5’);
111.8 (C-4);
123.9 (C-3);
152.2 (C-2);
157.7 (C-5);
177.6 (CON);
178.3 (CH=O).
HRMS: 210.07605 (C10H12NO4; calc. 210.07608).
ESI-MS-MS (cid=65) (rel. int.%): 192(100); 164(8); 126(2); 109(4).
Mp.: 169˚C - 172˚C (lit.: 171˚C - 172˚C [1] ).
IR νmax(KBr, cm−1): 3321, 3176, 3117, 2965, 2896, 2863, 2790, 2763, 1772, 1709, 1666, 1531, 1463, 1412, 1389, 1338, 1284, 1276, 1262, 1250, 1208, 1201, 1177, 1096, 1062, 1030, 1007.
1H NMR (400 MHz, DMSO-d6)
δH 1.86 - 1.95 (m, 1H, Hx-4’);
2.01 - 2.10 (m, 1H, Hx-3’);
2.16 - 2.34 (m, 2H, Hy-4’, Hy-3’);
4.49 + 4.58 (AB, 2 × 1H, Jgem = 13.2 Hz, CHO);
5.02 (m, 1H, H-5’);
6.73 (d, 1H, J = 3.4 Hz, H-4);
7.51 (d, 1H, J = 3.4 Hz, H-3);
8.80 (s, 1H, NH);
9.58 (s, 1H, CH=O).
13C NMR (100 MHz, DMSO-d6)
δC 27.5 (C-4’);
27.9 (C-3’);
60.3 (CH2O);
85.2 (C-5’);
111.8 (C-4);
123.9 (C-3);
152.2 (C-2);
157.7 (C-5);
177.6 (CON);
178.3 (CH=O).
HRMS: 210.07605 (C10H12NO4; calc. 210.07608).
ESI-MS-MS (cid=65) (rel. int.%): 192(100); 164(8); 126(2); 109(4).
International Journal of Organic Chemistry
Vol.04 No.05(2014), Article ID:52662,4 pages
10.4236/ijoc.2014.45033
Vol.04 No.05(2014), Article ID:52662,4 pages
10.4236/ijoc.2014.45033
The First Synthesis of Sessiline
Viktor Ilkei1, Kornél Faragó1, Zsuzsanna Sánta2, Miklós Dékány2, László Hazai1, Csaba Szántay Jr.2, Csaba Szántay1, György Kalaus1*
1Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary
2Gedeon Richter Plc, Budapest, Hungary
Email: *kalaus@mail.bme.hu
Copyright © 2014 by authors and Scientific Research Publishing Inc.
This work is licensed under the Creative Commons Attribution International License (CC BY).
http://creativecommons.org/licenses/by/4.0/
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