Abstract

There is disclosed an improved process for the racemization of (R)-α-ethyl-2-oxo-1-pyrrolidineacetic acid in a solution of alkali hydroxide. The process comprises heating a crystalline suspension of the racemic (RS)-α-ethyl-2-oxo-1-pyrrolidineacetic acid at a temperature from 100 °C to 250 °C to increase the yield and purity. The racemic (RS)-α-ethyl-2-oxo-1-pyrrolidineacetic acid is optically resolved into (S)-α-ethyl-2-oxo-1-pyrrolidineacetic acid and converted to levetiracetam.

IPC Classes  ?

• C01F 17/10 - Preparation or treatment, e.g. separation or purification
• C01F 17/20 - Compounds containing only rare earth metals as the metal element
• B01D 11/04 - Solvent extraction of solutions which are liquid
• C01F 17/17 - Preparation or treatment, e.g. separation or purification involving a liquid-liquid extraction

Abstract

There is disclosed an improved process for the racemization of (R)-α-ethyl-2-oxo-1-pyrrolidineacetic acid in a solution of alkali hydroxide. The process comprises heating a crystalline suspension of the racemic (RS)-α-ethyl-2-oxo-1-pyrrolidineacetic acid at a temperature from 100° C. to 250° C. to increase the yield and purity. The racemic (RS)-α-ethyl-2-oxo-1-pyrrolidineacetic acid is optically resolved into(S)-α-ethyl-2-oxo-1-pyrrolidineacetic acid and converted to levetiracetam.

IPC Classes  ?

• C07D 207/27 - 2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom

Abstract

There is disclosed a process for the optical resolution of (RS)-α-ethyl-2-oxo-1- pyrrolidineacetic acid with a chiral amine and an optically inactive amine to form an ionic liquid in a solvent to produce (S)-α-ethyl-2-oxo-1-pyrrolidineacetic acid. The (S)-α-ethyl-2-oxo-1- pyrrolidineacetic acid is converted to (S)-α-ethyl-2-oxo-1-pyrrolidineacetamide.

IPC Classes  ?

• C01F 17/10 - Preparation or treatment, e.g. separation or purification
• C01F 17/20 - Compounds containing only rare earth metals as the metal element
• B01D 11/04 - Solvent extraction of solutions which are liquid
• C01F 17/17 - Preparation or treatment, e.g. separation or purification involving a liquid-liquid extraction

Abstract

488 to produce (S)-α-ethyl-2-oxo-1-pyrrolidineacetic acid. The (S)-α-ethyl-2-oxo-1-pyrrolidineacetic acid is converted to (S)-α-ethyl-2-oxo-1-pyrrolidineacetamide.

IPC Classes  ?

• C01F 17/10 - Preparation or treatment, e.g. separation or purification
• C01F 17/20 - Compounds containing only rare earth metals as the metal element
• B01C 11/04 -
• C01F 17/17 - Preparation or treatment, e.g. separation or purification involving a liquid-liquid extraction

Abstract

466 to produce (S)-α-ethyl-2-oxo-1-pyrrolidineacetic acid. The (S)-α-ethyl-2-oxo-1-pyrrolidineacetic acid is converted to (S)-α-ethyl-2-oxo-1-pyrrolidineacetamide.

IPC Classes  ?

• C01F 17/10 - Preparation or treatment, e.g. separation or purification
• C01F 17/20 - Compounds containing only rare earth metals as the metal element
• B01D 11/04 - Solvent extraction of solutions which are liquid
• C01F 17/17 - Preparation or treatment, e.g. separation or purification involving a liquid-liquid extraction

Abstract

There is disclosed a process for the optical resolution of (RS)-α-ethyl-2-oxo-1-pyrrolidineacetic acid with a chiral amine in a mixed solvent of aromatics and alkyl alcohol of C4-C8 to produce (S)-α-ethyl-2-oxo-1-pyrrolidineacetic acid. The (S)-α-ethyl-2-oxo-1-pyrrolidineacetic acid is converted to (S)-α-ethyl-2-oxo-1-pyrrolidineacetamide.

IPC Classes  ?

• C07D 207/27 - 2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom

Abstract

There is disclosed a process for the optical resolution of (RS)-α-ethyl-2-oxo-1-pyrrolidineacetic acid with a chiral amine in a solvent comprising an alkyl alcohol of C4-C6 to produce (S)-α-ethyl-2-oxo-1-pyrrolidineacetic acid. The (S)-α-ethyl-2-oxo-1-pyrrolidineacetic acid is converted to (S)-α-ethyl-2-oxo-1-pyrrolidineacetamide.

IPC Classes  ?

• C07D 207/27 - 2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom

Abstract

There is disclosed a process for the optical resolution of (RS)-α-ethyl-2-oxo-1-pyrrolidineacetic acid with a chiral amine and an optically inactive amine to form an ionic liquid in a solvent to produce (S)-α-ethyl-2-oxo-1-pyrrolidineacetic acid. The (S)-α-ethyl-2-oxo-1-pyrrolidineacetic acid is converted to (S)-α-ethyl-2-oxo-1-pyrrolidineacetamide.

IPC Classes  ?

• C07D 207/27 - 2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom

Abstract

There is disclosed a process for the production of levetiracetam by crystallizing levetiracetam in an aqueous solution, optionally in the presence of a water-soluble solvent. The product of levetiracetam contains no residual organic solvent.

IPC Classes  ?

• C07D 207/27 - 2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom

Abstract

There is disclosed a process for the production of levetiracetam comprising the conversion of (-)-(S)-alpha-ethyl-2-oxo-1-pyrrolidineacetic acid to (-)-(S)-aipha-ethyl-2-oxo-1-pyrrolidineacetic acid methyl ester, wherein the methyl ester derivative undergoes ammonolysis in an aqueous solution to afford levetiracetam. The process for purification comprising crystallizing levetiracetam in an aqueous solution, optionally in the presence of a water-soluble solvent, wherein levetiracetam contains no residual organic solvent.

IPC Classes  ?

• C07D 207/27 - 2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
• C07D 207/12 - Oxygen or sulfur atoms
• C07D 207/267 - 2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom

Abstract

There is disclosed a method for preparing levetiracetam and intermediates from a compound of the formula: There is disclosed a method for preparing levetiracetam and intermediates from a compound of the formula: There is disclosed a method for preparing levetiracetam and intermediates from a compound of the formula: wherein CR is selected from the group consisting of cyano, carboxylic acid, carboxamide, alkali carboxylate, alkaline earth metal carboxylate, alkyl carboxylate, and a mixture thereof.

IPC Classes  ?

• C07D 207/267 - 2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom

Abstract

There is disclosed a method for preparing levetiracetam and intermediates from a compound of the formula: wherein CR is selected from the group consisting of cyano, carboxylic acid, carboxamide, alkali carboxylate, alkaline earth metal carboxylate, alkyl carboxylate, and a mixture thereof.

IPC Classes  ?

• C07C 253/30 - Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
• C07D 207/27 - 2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
• C07C 255/03 - Mononitriles