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. R_f 0.47 (acetone:hexane = 2:1).
Mp.: 169˚C - 172˚C (lit.: 171˚C - 172˚C [1] ).

IR ν_max(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) 
δ_H 1.86 - 1.95 (m, 1H, H_x-4’); 
2.01 - 2.10 (m, 1H, H_x-3’); 
2.16 - 2.34 (m, 2H, H_y-4’, H_y-3’); 
4.49 + 4.58 (AB, 2 × 1H, J_gem = 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) 
δ_C 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 Kalaus^1*

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/

Budapest University of Technology and Economics
Budapesti Műszaki és Gazdaságtudományi Egyetem
Latin: Universitas Budapestinensis Scientiarum Technicarum et Oeconomicarum

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









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(±)-Methyl 2-[hydroxy(2-nitrophenyl)methyl]prop-2-enoate

¹H NMR (500 MHz, CDCl₃):  
δ 7.94 (dd, J 1.2/8.2 Hz, 1H), 
7.78 (d, 1H, J 7.9 Hz), 
7.61-7.67 (m, 1H), 
7.41-7.48 (m, 1H), 
6.36 (s, 1H), 
6.20 (s, 1H), 
5.72 (s, 1H), 
3.73 (s, 3H), 
3.08 (s, 1H, OH);

¹³C NMR (125 MHz, CDCl₃):  
δ 166.3, 
148.2, 
140.7, 
136.0, 
133.4, 
128.8, 
128.6, 
126.4, 
124.5, 
67.6, 
52.1;

(±)-Methyl 2-[hydroxy(2-nitrophenyl)methyl]prop-2-enoate (3): 92% yield, pale yellow oil; IR (film) ν_max/cm^-1: 3469, 1716, 1630, 1528, 1352;  

¹H NMR (500 MHz, CDCl₃): δ 7.94 (dd, J 1.2/8.2 Hz, 1H), 7.78 (d, 1H, J 7.9 Hz), 7.61-7.67 (m, 1H), 7.41-7.48 (m, 1H), 6.36 (s, 1H), 6.20 (s, 1H), 5.72 (s, 1H), 3.73 (s, 3H), 3.08 (s, 1H, OH);

¹³C NMR (125 MHz, CDCl₃): δ 166.3, 148.2, 140.7, 136.0, 133.4, 128.8, 128.6, 126.4, 124.5, 67.6, 52.1; 

HRMS (ESI TOF) 

Calcd. for C₁₁H₁₁NO₅[M + Na⁺]: 260.0529. Found: 260.0530.

J. Braz. Chem. Soc. vol.22 no.8 São Paulo Aug. 2011

http://dx.doi.org/10.1590/S0103-50532011000800022

http://www.scielo.br/scielo.php?pid=S0103-50532011000800022&script=sci_arttext 


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C-aryl glucoside SGLT2 inhibitors and method US 6515117 B2

Dapagliflozin

http://www.google.co.in/patents/US6515117

HPLC retention time: 7.08 min, 94% pure, YMC S5 C-18 4.6×50 mm column, 2.5 mL/min, detection at 220 nM; 8 min gradient 0-100% B hold 5 min at 100% B. Solvent A: 10% MeOH/H₂O+0.2% H₃PO₄. Solvent B: 90% MeOH/H₂O+0.2% H₃PO₄.

¹H NMP (500 MHz, CD₃OD) δ7.33 (d, 1H, J=6 Hz), 7.31 (d, 1H, J=2.2 Hz), 7.31 (dd, 1H, J=6 Hz, J=2.2 Hz), 7.07 (d, 2H, J=8.8 Hz), 6.78 (d, 2H, J=8.8 Hz), 4.07-3.90 (m, 7H), 3.85 (d, 1H, J=10.6 Hz), 3.69 (dd, 1H, J=5.3, 10.6 Hz), 3.42-3.25 (m, 4H) Hz), 1.34 (t, 3H, J=7 Hz).

¹³C NMP (125 MHz, CD₃OD) δ158.8, 140.0, 139.9, 134.4, 132.9, 131.9, 130.8, 130.1, 128.2, 115.5, 82.9, 82.2, 79.7, 76.4, 71.9, 64.5, 63.1, 39.2, 15.2.

Anal Calcd for C₂₁H₂₅ClO₆ LC-MS [M+Na⁺]431; found 431.

Dapagliflozin

Systematic (IUPAC) name
(2S,3R,4R,5S,6R)-2-[4-chloro-3-(4-ethoxybenzyl)phenyl]-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Clinical data
Trade names	Forxiga, Farxiga
AHFS/Drugs.com	UK Drug Information
Licence data	EMA:Link, US FDA:link
Pregnancy cat.	US: C
Legal status	UK: POM US: ℞-only
Routes	Oral
Identifiers
CAS number	461432-26-8
ATC code	A10BX09
PubChem	CID 9887712
ChemSpider	8063384
UNII	1ULL0QJ8UC
ChEMBL	CHEMBL429910
Synonyms	BMS-512148
Chemical data
Formula	C21H25ClO6
Mol. mass	408.873 g/mol

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