74046-07-4

Usage

Uses

Vigabatrin is a novel anti-epileptic drug. Antidepressant; antipsychotic; anxiolytic.

Biochem/physiol Actions

γ-Vigabatrin has the potential to treat infantile spasms and seizures. It exhibits therapeutic effects against cocaine and other addictions.

InChI:InChI=1/C6H11NO2/c1-2-5(7)3-4-6(8)9/h2,5H,1,3-4,7H2,(H,8,9)/t5-/m1/s1

Upstream product

• 93288-23-4 (5S)-5-ethenyl-2-pyrrolidinone 
• 139694-78-3 (S)-(-)-5-ethenyl-1-butenyl-2-pyrrolidinone 
• 148073-34-1 (S)-ethyl 4--5-hexenoate 
• 916677-49-1 C₁₃H₁₇NO₄S 
• 572889-82-8 (1R,5R,6R)-2-tert-butyl 6-methyl 2-azabicyclo[3.1.0]hex-3-ene-2,6-dicarboxylate 
• 149387-02-0 (5S)-5-(2-methylthioethyl)-2-pyrrolidinone 
• 151929-40-7 ethyl (4R)-4-(benzyloxycarbonylamino)-6-methylthio-2-hexenoate 
• 7440-44-0 pyrographite 
• 213693-00-6 (S)-4-Acetylamino-hex-5-enoic acid 
• 1099752-69-8 methyl (-)-(4S)-4-[bis(tert-butoxycarbonyl)amino]hex-5-enoate 
• 60643-86-9 4-amino-5-hexenoic acid 
• 916677-41-3 (S)-4-amino-5-hexenoic acid hydrochloride 
• 611182-50-4 (S)-4-(2,2,2-Trichloro-acetylamino)-hex-5-enoic acid methyl ester 
• 7149-65-7 ethyl (S)-pyroglutamate 

Downstream Products

• 526-63-6 (-)-isoretronecanol 

Relevant academic research and scientific papers

Scalable Synthesis of Both Enantiomers of Vigabatrin, an Antiepileptic Drug

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.

Resolution of racemic Vigabatrin using tartaric acid

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

Enantioselective iridium-catalyzed allylic aminations of allylic carbonates with functionalized side chains. Asymmetric total synthesis of (S)-vigabatrin

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

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

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

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.

Catalytic asymmetric rearrangement of allylic trichloroacetimidates. A practical method for preparing allylic amines and congeners of high enantiomeric purity

COP-Cl catalyzes the rearrangement of (E)-allylic trichloroacetimidates to provide transposed allylic trichloroacetamides of high enantiopurity, a transformation that underlies the first truly practical method for transforming prochiral allylic alcohols t

A short synthesis of γ-amino acids from nitrones; synthesis of Vigabatrin

Treatment of the γ-N-hydroxylamino-α,β-acetylenic esters, obtained by the reaction of nitrones with alkyl 3-lithiopropiolates, with H2 over Raney nickel, followed by in situ protection of the formed amines, gives N-Boc-γ-amino esters. This meth

Asymmetric Radical Cyclization With Pyroglutamate: Synthesis of 7-Substituted Pyrrolizidinones

Chiral, non-racemic N-(2-iodoethyl)-5-vinylpyrrolidin-2-ones have been synthesized and then cyclized with tributyltin hydride and azoisobutyronitrile (AIBN) to produce chiral, non-racemic pyrrolizidin-2-ones, with high diastereoselectivity.Reduction of the lactam moiety provides a facile route to naturally occuring pyrrolizidine alkaloids.