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/
The "K", central building looking from the river Danube before its renovation
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary
budapest
central market budapest
DRUG APPROVALS BY DR ANTHONY MELVIN CRASTO .....FOR BLOG HOME CLICK HERE
| Budapest University of Technology and Economics | |
|---|---|
| Budapesti Műszaki és Gazdaságtudományi Egyetem | |
 | |
| Latin: Universitas Budapestinensis Scientiarum Technicarum et Oeconomicarum |
budapest
central market budapest
DRUG APPROVALS BY DR ANTHONY MELVIN CRASTO .....FOR BLOG HOME CLICK HERE
Join me on twitter
Join me on google plus 
Googleplus
Googleplus
No comments:
Post a Comment