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US 12,559,456 B2Granted
Method for preparing levetiracetam and intermediates thereof
AssigneeSuzhou Brighthope Pharma Tech Co., Ltd
InventorSongzhou Hu
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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.
Claims3
A process for producing (S)-α-ethyl-2-oxo-1-pyrrolidineacetamide of formula (I),
- comprising:
- (a) converting a compound of formula (II)
- to (RS)-α-ethyl-2-oxo-1-pyrrolidineacetic acid of formula (IV):
- 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;
- the alkali is lithium, sodium, potassium, or a mixture thereof;
- the alkaline earth metal is magnesium, calcium, barium, or a mixture thereof;
- and the alkyl is C1-C12;
- (b) resolving the (RS)-α-ethyl-2-oxo-1-pyrrolidineacetic acid of step (a) into optically active (S)-α-ethyl-2-oxo-1-pyrrolidineacetic acid of formula (V):
- and
- (c) subjecting the (S)-α-ethyl-2-oxo-1-pyrrolidineacetic acid of formula (V) of step (b) to an amidation reaction to form (S)-α-ethyl-2-oxo-1-pyrrolidineacetamide of formula (I).
7 more elements
A process for producing (S)-α-ethyl-2-oxo-1-pyrrolidineacetamide of formula (I),
- comprising:
- (a) converting a compound of formula (II)
- to (RS)-α-ethyl-2-oxo-1-pyrrolidineacetic acid ester of formula (VI):
- 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;
- the alkali is lithium, sodium, potassium, or a mixture thereof;
- the alkaline earth metal is magnesium, calcium, barium, or a mixture thereof;
- the alkyl is C1-C12;
- and R1 is C1-C12;
- (b) resolving the (RS)-α-ethyl-2-oxo-1-pyrrolidineacetic acid ester of step (a) to optically active (S)-α-ethyl-2-oxo-1-pyrrolidineacetic acid of formula (V):
- with a lipase;
- and
- (c) subjecting the (S)-α-ethyl-2-oxo-1-pyrrolidineacetic acid of formula (V) to an amidation reaction to form (S)-α-ethyl-2-oxo-1-pyrrolidineacetamide of formula (I).
9 more elements
A process for producing (S)-α-ethyl-2-oxo-1-pyrrolidineacetamide of formula (I),
- comprising:
- (a) converting a compound of formula (II)
- to (RS)-α-ethyl-2-oxo-1-pyrrolidineacetic acid ester of formula (VI):
- 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;
- the alkali is lithium, sodium, potassium, or a mixture thereof;
- the alkaline earth metal is magnesium, calcium, barium, or a mixture thereof;
- the alkyl is C1-C12;
- and R1 is C1-C12;
- (b) resolving the (RS)-α-ethyl-2-oxo-1-pyrrolidineacetic acid ester of step (a) into (S)-α-ethyl-2-oxo-1-pyrrolidineacetic acid ester of formula (VII):
- with a lipase;
- and
- (c) subjecting the (S)-α-ethyl-2-oxo-1-pyrrolidineacetic acid ester of formula (VII) to an amidation reaction to form (S)-α-ethyl-2-oxo-1-pyrrolidineacetamide of formula (I).
9 more elements
Dependencies are inferred from the claim text.