170450-74-5

Usage

Uses

Used in Organic Synthesis:
2,6-Piperidinedione, 3-ethyl-3-(4-nitrophenyl)-, (3R)serves as a valuable building block in organic synthesis. Its versatile structure allows for the creation of a wide range of chemical compounds, making it a useful precursor in the synthesis of various organic molecules.
Used in Pharmaceutical Research:
2,6-Piperidinedione, 3-ethyl-3-(4-nitrophenyl)-, (3R)is utilized in pharmaceutical research for the development of new drugs. Its unique structural and chemical properties make it a promising candidate for the design and synthesis of novel therapeutic agents. The presence of the nitrophenyl group further enhances its potential in drug discovery, as it can be used to study chemical reactions and interactions in biological systems.
Used in Biomedical Research:
2,6-Piperidinedione, 3-ethyl-3-(4-nitrophenyl)-, (3R)also has potential applications in biomedical research. Its structural features and chemical properties make it a valuable tool for studying various biological processes and mechanisms. 2,6-Piperidinedione, 3-ethyl-3-(4-nitrophenyl)-, (3R)can be used to investigate the interactions between molecules and biological systems, contributing to a better understanding of disease pathways and the development of targeted therapies.

Upstream product

• 100-00-5 4-chlorobenzonitrile 
• 30698-33-0 methyl 2-cyano-2-(4-nitrophenyl)acetate 
• 94814-82-1 2-(4-nitrophenyl)butanonitrile 
• 170450-66-5 (S)-Ethyl 2-formyl-2-<(formyloxy)methyl>phenylpropionate 
• 170450-68-7 (S)-Diethyl 4-phenyl-4-<(formyloxy)methyl>glutaconate 
• 170450-69-8 (S)-Diethyl 2-phenyl-2-(hydroxymethyl)glutarate 
• 170450-70-1 (S)-Diethyl 2-phenyl-2-formylglutarate 
• 170450-72-3 (R)-Diethyl 2-phenyl-2-ethylglutarate 
• 170450-71-2 (R)-Diethyl 2-phenyl-2-vinylglutarate 
• 170450-61-0 4,5-Dioxo-3-phenyl-tetrahydro-furan-3-carboxylic acid ethyl ester 
• 17575-58-5 glutethimide 
• 170450-62-1 (3S,4R)-4-Hydroxy-5-oxo-3-phenyl-tetrahydro-furan-3-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Production of (R)-aminoglutethimide: A new route from 1 -chloro-4-nitrobenzene

The development of a short, safe and enantioselective route for the preparation of (R)-aminoglutethimide is described. The process was designed for economic large-scale manufacture of the bulk drug substance to acceptable quality standards, to allow clinical evaluation of the single enantiomer over the existing racemate. (R)-Aminoglutethimide was prepared from 1-chloro-4-nitrobenzene using a six-stage synthetic sequence, via chemoresolution of key intermediate racemic 4-cyano-4-(4-nitrophenyl)hexanoic acid using (-)-cinchonidine. The process allowed for preparation of several kilograms of the precursor (R)-nitroglutethimide, to cGMP at pilot-plant scale, along with demonstration of the final hydrogenation step to (R)-aminoglutethimide in the laboratory. This route avoids the problems of hazardous nitration technology, and therefore regio-isomer contamination of the product, associated with other procedures. The resolution chemistry described represents an improvement on literature procedures. Optimisation of the asymmetric Michael addition offers an attractive alternative approach.

Resolution of 4-Cyano-4-(4-nitrophenyl)hexanoic acid: Synthesis of (R) and (S)-3-(4-aminophenyl)-3-ethylpiperidine- (aminoglutethimide)

Using (R)- or (S)-1-phenylethylamine as a resolving agent, (R)- and (S)-4-cyano-4-(4-nitrophenyl)hexanoic acids have been isolated. Cyclization of each enantiomer, followed by reduction of the nitro group, afforded (R)- and (S)-aminoglutethimide of high (>99% ee enantiomeric purity, respectively. The absolute configuration of (R)-(+)-3-(4-nitrophenyl)-3-ethylpiperidine-2,6-dione was solved by X-ray single crystal analysis thus establishing the (R)-configuration of the dextrorotatory aminoglutethimide. Attempted resolution of the other precursor of aminoglutethimide, 4-cyano-2-ethyl-(4-nitrophenyl)butanoic acid with (S)-1-phenylethylamine led to the formation of the double salt. Its crystal structure was elucidated by X-ray crystallographic analysis.