68506-86-5Relevant academic research and scientific papers
Resolution of racemic Vigabatrin using tartaric acid
Karumanchi, Kishore,Kumar Natarajan, Senthil,Moturu, Krishna Murthy V. R.,Chavakula, Ramadas,Korupolu, Raghu Babu,Bonige, Kishore Babu
, p. 2221 - 2225 (2018)
An efficient and simple resolution methodology for the preparation of (S)- and (R)-Vigabatrin has been developed. In addition, a method of preparation for the novel compounds Vigabatrin-l-tartarate and Vigabatrin-d-tartarate is also described. The title c
Scalable Synthesis of Both Enantiomers of Vigabatrin, an Antiepileptic Drug
Jachak, Gorakhnath R.,Reddy, D. Srinivasa
, p. 1257 - 1260 (2019)
Vigabatrin is a potent inhibitor of gamma-aminobutyric acid (GABA) catabolism used for the treatment of epilepsy. Here we have synthesized both enantiomers of the drug vigabatrin in five steps from known intermediates using Wittig olefination and pyrolytic elimination as key steps. The target compounds are synthesized in gram scale amounts with >98 % enantiopurity.
A convenient approach for vinylation reaction in the synthesis of 5-vinyl-2-pyrrolidinone, a key intermediate of vigabatrin
Karumanchi, Kishore,Natarajan, Senthil Kumar,Gadde, Sunil,Vanchanagiri, Krishna
, p. 2035 - 2039 (2020/01/02)
A convenient, safe and cost-effective method for carrying out the key vinylation of 5-ethoxy-2-pyrrolidinone (8) in the preparation of 5-vinyl-2-pyrrolidinone (2) in the presence of potassium carbonate is described. This present procedure is developed by replacing inherently hazardous ethyl magnesium bromide with inexpensive and eco-friendly potassium carbonate. The reaction was performed on a multi-gram scale, with vinyl magnesium bromide as the vinylation reagent, in an 81% yield to give the 5-vinyl-2-pyrrolidinone with excellent purity and without the need for chromatography.
Preparation method of aminohexenoic acid
-
Paragraph 0016; 0040; 0050; 0051; 0057; 0058; 0061-0064, (2020/02/14)
The invention discloses a preparation method of aminohexenoic acid, which is characterized by comprising the following steps: with diethyl malonate and 1,4-dichloro-2-butene as raw materials, preparing 2-vinylcyclopropane-1,1-dicarboxylic acid diethyl ester; then carrying out a reaction on 2-vinylcyclopropane-1,1-dicarboxylic acid diethyl ester in the presence of ammonia and formamide to prepare 2-carbonyl-5-vinyl-pyrrolidine-3-amide; preparing a 4-amino-5-hexenoic acid crude product from the 2-carbonyl-5-vinyl-pyrrolidine-3-amide under an acidic condition; then preparing triisopropylsilyl-4-aminohexyl-5-alkenyl ester from 4-amino-5-hexenoic acid and triisopropylchlorosilane in the presence of triethylamine and ammonia; recrystallizing the triisopropylsilyl-4-aminohexyl-5-alkenyl ester inchloroform/methanol to obtain a purified product of the triisopropylsilyl-4-aminohexyl-5-alkenyl ester; wherein the volume ratio of chloroform to methanol is 1:7; and hydrolyzing the purified productof the triisopropylsilyl-4-aminohexyl-5-alkenyl ester under an alkaline condition to obtain the aminohexylenic acid.
A PROCESS FOR THE PREPARATION OF VIGABATRIN
-
Page/Page column 5; 6, (2019/10/15)
The present invention provides a process for the preparation of vigabatrin of formula (I) comprising of dissolving vigabatrin in water, optionally treating with charcoal, filtering and adding an acid to the reaction mass followed by the addition of an organic solvent and then isolating vigabatrin of formula (I) with high purity.
Process for preparing 4-amino-5-hexenoic acid from succinimide
-
Page/Page column 9, (2013/02/28)
The present invention relates to a competitive process for the preparation of 4-amino-5-hexenoic acid and intermediates thereof. This compound is a well-known anti-epileptic drug for which several syntheses have been developed, all of them presenting drawbacks. The preparation process according to the present invention is very competitive from an economical point of view and is adapted to industrial scale preparation of 4-amino-5-hexenoic acid.
Enantioselective iridium-catalyzed allylic aminations of allylic carbonates with functionalized side chains. Asymmetric total synthesis of (S)-vigabatrin
Gnamm, Christian,Franck, Geraldine,Miller, Nicole,Stork, Timon,Broedner, Kerstin,Helmchen, Guenter
experimental part, p. 3331 - 3350 (2009/05/27)
Indium-catalyzed aminations of allylic carbonates containing a variety of O-functional groups have been explored. High degrees of regio- as well as enantioselectivity were achieved with diacylamides under salt-free conditions and with arylamines. The results allowed the antiepilepsy drug (5)-vigabatrin to be prepared via a very short route.
Asymmetric synthesis of (S)-vigabatrin and (S)-dihydrokavain via cobalt catalyzed hydrolytic kinetic resolution of epoxides
Paul Raj, I. Victor,Sudalai
, p. 2646 - 2648 (2008/09/19)
A concise route to the asymmetric synthesis of (S)-vigabatrin and (S)-dihydrokavain has been described using Co-catalyzed hydrolytic kinetic resolution of racemic epoxides and regiospecific opening of terminal epoxides with dimethylsulfonium me
Synthesis of vigabatrin
Chang, Meng-Yang,Lin, Chun-Yu,Ong, Chi-Wi
, p. 2031 - 2036 (2008/01/27)
A concise synthesis of vigabatrin has been achieved from trans-(2S,4R)-4-hydroxyproline via the key regioselective Baeyer-Villiger lactonization reaction.
Synthesis of functionalized pyrrolidin-2-ones and (S)-vigabatrin from pyrrole
Gheorghe, Alexandru,Schulte, Michael,Reiser, Oliver
, p. 2173 - 2176 (2007/10/03)
Starting from pyrrole, the novel 3,4-didehydropyrohomoglutamate 8 or (ent)-8 can be efficiently synthesized in up to 91% ee, which can be utilized as a versatile building block toward functionalized pyrrolidin-2-ones. Moreover, (ent)-8 can be readily converted to (S)-Vigabatrin, being an irreversible inhibitor for GABA-T, which is used as adjunctive therapy in patients that suffer from epilepsy.
