102849-49-0

Usage

Chemical Properties

White Solid

Uses

Levetiracetam intermediate.

InChI:InChI=1/C8H13NO3/c1-2-6(8(11)12)9-5-3-4-7(9)10/h6H,2-5H2,1H3,(H,11,12)/t6-/m0/s1

Upstream product

• 616-45-5 2-pyrrolidinon 
• 2681-94-9 (2R)-2-bromobutanoic acid 
• 909566-58-1 1-((S)-1-hydroxybutane-2-yl)pyrrolidin-2-one 
• 1004767-63-8 (-)-(S)-alpha-ethyl-2-oxo-1-pyrrolidineacet-N-(+)-(R)-(1-phenylethyl)-amide 
• 96-48-0 4-butanolide 
• 5856-62-2 (S)-2-aminobutan-1-ol 
• 86815-10-3 ethyl 2-(2-oxo-1-pyrrolidinyl)butyrate 
• 1415316-37-8 (S)-1-(1-(benzyloxy)butan-2-yl)pyrrolidine-2,5-dione 
• 358629-39-7 (Z)-2-(2-oxopyrrolidin-1-yl)-2-butenoic acid 
• 102916-46-1 (S)-α-ethyl-2-oxo-1-pyrrolidineacetic acid (R)-α-methylbenzylamine salt 
• 67118-31-4 α-ethyl-2-oxo-1-pyrrolidineacetic acid, 
• 912643-33-5 (S)-1-(1-(benzyloxy)butan-2-yl)pyrrolidin-2-one 
• 873786-87-9 (αS,3S)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl 2-(2-oxopyrrolidin-1-yl)butyrate 

Downstream Products

• 102767-28-2 levetiracetam 
• 358629-51-3 (S)-methyl 2-(2-oxopyrrolidin-1-yl)-2-butanoate 

Relevant academic research and scientific papers

Scalable Flow Electrochemical Alcohol Oxidation: Maintaining High Stereochemical Fidelity in the Synthesis of Levetiracetam

An electrochemical flow process has been developed for an alcohol oxidation step in the synthesis of the generic epilepsy drug levetiracetam. A crucial metric in this process is the retention of high enantiomeric purity as the oxidation of the primary alcohol to the carboxylic acid proceeds via an epimerizable aldehyde intermediate. Here, three different reactor configurations are compared: undivided batch, undivided flow, and divided flow cells. The divided flow cell accesses the highest rate, throughput, and enantiomeric fidelity among the three configurations. This approach is showcased in a 200-g scale process that retains ≥97% enantiomeric purity and highlights a unique advantage of flow electrolysis.

Preparation method of levetiracetam and intermediates thereof

The invention provides a preparation method of levetiracetam and intermediates thereof. The specific steps are as follows: dropwise adding pyrrolidone into a toluene solution of sodium methoxide or sodium hydride, performing concentrating to dryness after a reaction is completed, adding toluene again, dropwise adding ethyl 2-bromobutyrate, and carrying out a reaction by heating to obtain a compound of a formula 3; adding a NaOH aqueous solution to the compound of the formula 3, performing heating until a reaction is completed, and dropwise adding concentrated hydrochloric acid to precipitate acompound of a formula 4; carrying out a reaction of the compound of the formula 4, R-(+)-phenylethylamine, and triethylamine to obtain a compound of a formula 6; performing hydrolysis by a NaOH solution, acidification by concentrated hydrochloric acid, and purification to a compound of a formula 7; and performing esterification by TsOH/EtOH to obtain a compound of a formula 8, and then performingammonia hydrolysis to obtain levetiracetam.

Total synthesis of levetiracetam

Total synthesis of levetiracetam, an active ingredient of epilepsy treatment medications, is reported. The reported method is based on a one-pot dehydration/sigmatropic rearrangement of (R,E)-hept-4-en-3-ol carbamate to the corresponding allylamine derivative, an advanced precursor of levetiracetam.

Sequential ruthenium catalysis for olefin isomerization and oxidation: Application to the synthesis of unusual amino acids

How can you use a ruthenium isomerization catalyst twice? A ruthenium-catalyzed sequence for the formal two-carbon scission of allyl groups to carboxylic acids has been developed. The reaction includes an initial isomerization step using commercially available ruthenium catalysts followed by in situ transformation of the complex to a metal-oxo species, which is capable of catalyzing subsequent oxidation reactions. The method enables enantioselective syntheses of challenging α-tri- and tetrasubstituted α-amino acids including an expedient total synthesis of the antiepileptic drug levetiracetam.

Compositions and methods for the treatment of epilepsy

The invention relates to the compounds of formula I and formula II or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula I or formula II; and methods for treating or preventing neurological diseases may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of epilepsy, bipolar disorder, trigeminal neuralgia, attention-deficit hyperactivity disorder, partial seizures, adjunctive therapy for partial, myoclonic, tonic-clonic seizures and schizophrenia, neuropathic pain, seizures, Tourette syndrome, Alzheimer's disease, autism, bipolar disorder and anxiety disorder, bipolar disorder, mania, phantom limb syndrome, complex regional pain syndrome, paroxysmal extreme pain disorder, neuromyotonia, intermittent explosive disorder, borderline personality disorder, myotonia congenita and post-traumatic stress disorder.

An alternate synthesis of enantiomerically pure levetiracetam (Keppra)

A simple and efficient synthesis of levetiracetam has been achieved with high enantiopurity (>99%) starting from commercially available benzyl glycidyl ether. The method is amenable for industrial scale-up.

An alternate synthesis of enantiomerically pure levetiracetam (Keppra)

A simple and efficient synthesis of levetiracetam has been achieved with high enantiopurity (>99%) starting from commercially available benzyl glycidyl ether. The method is amenable for industrial scale-up.

Enantioselective access to chiral drugs by using asymmetric hydrogenation catalyzed by Rh(P-OP) complexes

P-OP art: Rhodium complexes of P-OP ligands serve as highly efficient and enantioselective catalysts in asymmetric hydrogenation leading to various valuable pharmaceutical building blocks and several direct precursors of chiral drugs such as LY2497282, la

Asymmetric synthesis of the antiepileptic drug levetiracetam

Palladium-catalyzed asymmetric synthesis of levetiracetam of antiepileptic drug was expediently accomplished.

PROCESSES FOR THE PREPARATION OF LEVETIRACETAM

Provided are processes for preparing levetiracetam of the Formula (I):Various aspects and embodiments are provided.