99735-46-3

Usage

Uses

Used in Pharmaceutical Industry:
(S)-Methyl 5-oxo-1-((R)-1-phenylethyl)pyrrolidine-3-carboxylate is used as a chiral building block for the synthesis of pharmaceutical compounds. Its unique stereochemistry allows for the creation of enantiomerically pure drugs, which can have different biological activities and reduce potential side effects.
Used in Chemical Industry:
(S)-Methyl 5-oxo-1-((R)-1-phenylethyl)pyrrolidine-3-carboxylate is used as an intermediate in the synthesis of various organic compounds. Its reactivity and functional groups make it a versatile component in the production of specialty chemicals, agrochemicals, and other fine chemicals.
Further research and testing are needed to fully understand the properties and potential uses of (S)-Methyl 5-oxo-1-((R)-1-phenylethyl)pyrrolidine-3-carboxylate, as its applications may extend beyond the current understanding.

Upstream product

• 2627-86-3 (S)-1-phenyl-ethylamine 
• 617-52-7 Dimethyl itakonate 
• 97-65-4 2-methylenesuccinic acid 
• 67-56-1 methanol 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 915302-94-2 (3RS)-1-<(R)-1-phenylethyl>-5-oxo-3-pyrrolidinecarboxylic acid 

Downstream Products

• 124391-76-0 -(+)-methanol 
• 949149-62-6 (S)-benzyl-1-((R)-1-phenylethyl)-5-thioxopyrrolidine-3-carboxylate 
• 949149-64-8 (3S)-benzyl-1-[(R)-1-phenylethyl]pyrrolidine-3-carboxylate 
• 72580-53-1 (S)-(+)-3-pyrrolidinecarboxylic acid 
• 865362-97-6 (1R,3S)-5-(2-oxo-2-phenyl-ethylidene)-1-(1-phenyl-ethyl)-pyrrolidine-3-carboxylic acid methyl ester 
• 110013-19-9 (S)-(-)-3-(hydroxymethyl)pyrrolidine 
• 109960-57-8 Ethyl-[(R)-1-((R)-1-phenyl-ethyl)-pyrrolidin-3-ylmethyl]-amine 
• 1206669-45-5 (3S)-4-(1-hydroxy-1-methyl-ethyl)-2-oxo-1-[(1R)-phenylethyl]pyrrolidine 
• 199174-24-8 tert-butyl (3S)-3-(hydroxymethyl)pyrrolidine-1-carboxylate 
• 1264942-79-1 (3S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1-[(1R)-1-phenylethyl]pyrrolidine 
• 915795-08-3 C₁₅H₁₉NO₃ 
• 915795-07-2 C₁₅H₁₉NO₃ 
• 96449-93-3 (S)-5-Oxo-1-((R)-1-phenyl-ethyl)-pyrrolidine-3-carboxylic acid 
• 109960-55-6 (3S)-N-<(R)-phenylethyl>-3-(hydroxymethyl)pyrrolidine 

Relevant academic research and scientific papers

Design of novel HIV-1 protease inhibitors incorporating isophthalamide-derived P2-P3 ligands: Synthesis, biological evaluation and X-ray structural studies of inhibitor-HIV-1 protease complex

Based upon molecular insights from the X-ray structures of inhibitor-bound HIV-1 protease complexes, we have designed a series of isophthalamide-derived inhibitors incorporating substituted pyrrolidines, piperidines and thiazolidines as P2-P3 ligands for specific interactions in the S2-S3 extended site. Compound 4b has shown an enzyme Ki of 0.025 nM and antiviral IC50 of 69 nM. An X-ray crystal structure of inhibitor 4b-HIV-1 protease complex was determined at 1.33 ? resolution. We have also determined X-ray structure of 3b-bound HIV-1 protease at 1.27 ? resolution. These structures revealed important molecular insight into the inhibitor–HIV-1 protease interactions in the active site.

Synthesis and determination of absolute configuration of a non-peptidic αvβ6 integrin antagonist for the treatment of idiopathic pulmonary fibrosis

A diastereoselective synthesis of (S)-3-(3-(3,5-dimethyl-1H-pyrazol-1-yl)phenyl)-4-((R)-3-(2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl)pyrrolidin-1-yl)butanoic acid (1), a potential therapeutic agent for the treatment of Idiopathic Pulmonary Fibrosis, which is currently undergoing Phase I clinical trials is reported. The key steps in the synthesis involved alkylation of 2-methylnaphthyridine with (R)-N-Boc-3-(iodomethyl)-pyrrolidine, and an asymmetric Rh-catalysed addition of an arylboronic acid to a 4-(N-pyrrolidinyl)crotonate ester. The overall yield of the seven linear step synthesis was 8% and the product was obtained in >99.5% ee proceeding with 80% de. The absolute configuration of 1 was established by an alternative asymmetric synthesis involving alkylation of an arylacetic acid using Evans oxazolidinone chemistry, acylation using the resulting 2-arylsuccinic acid, and reduction. The absolute configuration of the benzylic asymmetric centre was established as (S).

PYRIMIDONE DERIVATIVES USED AS TAU PROTEIN KINASE 1 INHIBITORS

A compound represented by the formula (I) or a pharmaceutically acceptable salt thereof: wherein Z represents nitrogen atom or C-X; X represents hydrogen atom or fluorine atom; R1 is hydrogen atom or a C1 -C3 alkyl group; L represents single bond or a C1 -C6 alkylene group which may be substituted; Y represents single bond, sulfur atom, oxygen atom, NH, or the like; R2 represents hydrogen atom or a cyclic group which may be substituted, which is used for preventive and/or therapeutic treatment of a disease caused by abnormal activity of tau protein kinase 1 such as a neurodegenerative diseases (e.g. Alzheimer disease).

4-Piperidines and 3-pyrrolidines as dual serotonin and noradrenaline reuptake inhibitors: Design, synthesis and structure-activity relationships

Single enantiomer [(aryloxy)(pyridinyl)methyl]piperidine and pyrrolidine derivatives 5-9 are inhibitors of monoamine reuptake. Structure-activity relationships established that monoamine reuptake inhibition are functions of amine, pyridine isomer, aryloxy ring substitution and stereochemistry. Consequently, selective NRIs, selective SRIs, dual SNRIs and triple SNDRIs were all identified. Dual SNRIs 5l-a and 9c were evaluated in additional pharmacology and pharmacokinetic studies as representative examples from this series.

A rapid and convenient synthesis of β-proline

A short, reliable, and cheap synthesis of both enantiomers of β-proline, an efficient organocatalyst and an important building block in medicinal chemistry, has been developed in four steps (overall yield: 72%) from the diasteromeric adducts of methyl itaconate and (R)-α-methylbenzylamine. The key step involves the chemoselective reduction of a lactam group in the presence of a benzyl ester.

GABA Agonists and Uptake Inhibitors. Synthesis, Absolute Stereochemistry, and Enantioselectivity of (R)-(-)- and (S)-(+)-Homo-β-proline

The cyclic analogue of 4-aminobutyric acid (GABA), 3-pyrrolidineacetic acid (homo-β-proline), is a potent agonist at GABAA receptors, it interacts effectively with GABA-uptake mechanisms, and it is a moderately potent inhibitor of GABAB/s