DR ANTHONY MELVIN CRASTO,WorldDrugTracker, helping millions, A 90 % paralysed man in action for you, I am suffering from transverse mylitis and bound to a wheel chair, With death on the horizon, nothing will not stop me except God................DR ANTHONY MELVIN CRASTO Ph.D ( ICT, Mumbai) , INDIA 25Yrs Exp. in the feld of Organic Chemistry,Working for GLENMARK GENERICS at Navi Mumbai, INDIA. Serving chemists around the world. Helping them with websites on Chemistry.Million hits on google, world acclamation from industry, academia, drug authorities for websites, blogs and educational contribution

Tuesday 30 December 2014

The First Synthesis of Sessiline


Sessiline
[5-(5-oxo-pyrrolidin-2-yloxymethyl)-furan-2-carbaldehyde 


5-(5-oxo-pyrrolidin-2-yloxymethyl)-furan-2-carbaldehyde


http://file.scirp.org/Html/4-1020299_52662.htm



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.

1NMR (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
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
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/


Budapest University of Technology and Economics
Budapesti Műszaki és Gazdaságtudományi Egyetem
BME1782.svg
LatinUniversitas Budapestinensis Scientiarum Technicarum et Oeconomicarum
Budapest Tech Univ central K building.jpg


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


Join me on Linkedin

View Anthony Melvin Crasto Ph.D's profile on LinkedIn

Join me on Facebook FACEBOOK
Join me on twitterFollow amcrasto on Twitter     
Join me on google plus Googleplus

 amcrasto@gmail.com








No comments:

Post a Comment