62613-81-4

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 4-hydroxy-2-oxopyrrolidine-1-acetate is used as an impurity in the production of the nootropic drug Oxiracetam (O846905) for its potential cognitive-enhancing properties.

InChI:InChI=1/C8H13NO4/c1-2-13-8(12)5-9-4-6(10)3-7(9)11/h6,10H,2-5H2,1H3

Upstream product

• 62613-80-3 1-ethoxycarbonylmethylpyrrolidine-2,4-dione 
• 68252-20-0 4-Trimethylsilyloxy-1H-pyrrolidin-2one 
• 105-36-2 ethyl bromoacetate 
• 7664-93-9 sulfuric acid 
• 77191-37-8 4-hydroxy-2-oxo-1-pyrrolidine acetic acid 
• 110104-61-5 ethyl (2,5-dihydro-4-methoxy-2-oxo-1H-pyrrol-1-yl)acetate 
• 110853-09-3 ethyl (4-methoxy-2-oxopyrrolidin-1-yl)acetate 

Downstream Products

• 77191-37-8 4-hydroxy-2-oxo-1-pyrrolidine acetic acid 
• 68252-28-8 oxiracetam 
• 120428-80-0 N-(2-amino-2-oxoethyl)-2-(4-hydroxy-2-oxotetrahydropyrrol-1-yl)acetamide 

Relevant academic research and scientific papers

Oxiracetam preparation method

An oxiracetam preparation method comprises the following steps: (a) azidation reaction of 4-chloro-3-hydroxybutyrate as a starting material and an azidation reagent to obtain an give intermediate I; (2) reduction reaction of the intermediate I to obtain an intermediate II; (2) condensation reaction of the intermediate II and a halogenated acetic acid ester to obtain an intermediate III; (3) ring closing reaction of the intermediate III to obtain an intermediate IV; and (4) aminolysis reaction of the intermediate IV to obtain desired product oxiracetam. The desired product oxiracetam with an ideal yield of at least more than 38% can be obtained, and a new oxiracetam synthetic route is opened up.

Process for the production of 4-hydroxy-2-oxopyrrolidin-1-yl-acetamide

Process for the production of 4-hydroxy-2-oxoyrrolidin-1-yl-acetamide, a cerebrally active pharmaceutical agent. A 4-halo-3-alkoxy-butenoic acid ester is reacted with glycine to new intermediate products of the formula: STR1 There is further by acid hydrolysis of the alkoxy group, subsequent hydrogenation, esterification of the carboxyl function and finally conversion to the end product by reaction with ammonia.

Process for the production of 4-hydroxy-2-oxo-pyrrolidin-1-yl acetamide

Process for the production of 4-hydroxy-2-oxo-pyrrolidin-1-yl acetamide. A 4-(C1 -C2)-alkoxy-3-pyrrolin-2-on-1-yl-acetic acid (C1 -C4)-alkyl ester of the formula: STR1 wherein R1 is alkyl having 1 or 2 C atoms and R2 is alkyl having 1 to 4 C atoms, is reacted with either trichloromethylsilane in the presence of an alkali iodide or in an acid anhydrous medium to a 2,4-dioxo-pyrrolidin-1-yl-acetic acid (C1 -C4)-alkyl ester. The latter is optionally isolated and then hydrogenated with sodium borohydride to a 4-hydroxy-2-oxo-pyrrolidin-1-yl-acetic acid (C1 -C4)-alkyl ester. Finally, the 4-hydroxy-2-oxo-pyrrolidin-1-yl-acetic acid (C1 -C4)-alkyl ester is converted by amidation with ammonia to the desired end product.

Preparation of pyrrolidine and pyrrolidin-2-one derivatives

Preparation of compounds of the formula: STR1 wherein n is 1, 2 or 3, R1 and R2, which may be the same or different, are hydrogen or alkyl containing 1 to 3 carbon atoms and the asterisk indicates the center of asymmetry of the molecule, and compounds of the formula STR2 wherein R" is a saturated or unsaturated aliphatic hydrocarbon containing 1 to 6 carbon atoms, R3 is hydrogen or acyl containing 1 to 7 carbon atoms and the asterisk indicates the center of asymmetry of the molecule. The compounds produced by the present invention improve learning memory and display a protecting effect against the E.E.G. consequence of an overdose of barbiturates and against the reduced performance following brain damage (e.g. cerebral edema).