83541-81-5

Basic information

• Product Name: (S)-DiMethyl pyrrolidine-1,2-dicarboxylate
• Synonyms: (S)-DiMethyl pyrrolidine-1,2-dicarboxylate;(S)-dimethylpyrrolidine-1,2-dicarboxylate(WXC07915)
• CAS NO: 83541-81-5
• Molecular Formula: C₈H₁₃NO₄
• Molecular Weight: 187.19312
• Mol File: 83541-81-5.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (S)-DiMethyl pyrrolidine-1,2-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-DiMethyl pyrrolidine-1,2-dicarboxylate(83541-81-5)
• EPA Substance Registry System: (S)-DiMethyl pyrrolidine-1,2-dicarboxylate(83541-81-5)

Safety Data

• Hazardous Substances Data: 83541-81-5(Hazardous Substances Data)

Usage

General Description

(S)-DiMethyl pyrrolidine-1,2-dicarboxylate, also known as piracetam, is a synthetic chemical compound that belongs to the racetam class of drugs. It is a derivative of the neurotransmitter GABA and is believed to enhance cognitive function by modulating the activity of neurotransmitters in the brain. Piracetam has been studied for its potential to improve memory, learning, and overall cognitive function. It is also used in the treatment of cognitive disorders such as dementia and stroke. Additionally, piracetam has been found to have neuroprotective effects and has been studied for its potential to improve symptoms in conditions such as dyslexia and ADHD. However, its mechanism of action is not fully understood, and more research is needed to fully understand its effects and potential medical uses.

Upstream product

• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 79-22-1 methyl chloroformate 
• 147-85-3 L-proline 
• 88817-72-5 (S)-5-Methoxy-2,5-bis-methoxycarbonylamino-pentanoic acid methyl ester 
• 185385-13-1 1-carbomethoxy-5-methoxy-L-proline methyl ester 
• 147-85-3 L-proline 
• 158554-84-8 dimethyl (2S)-5-oxopyrrolidine-1,2-dicarboxylate 
• 93271-96-6 (2S,5RS)-1,2-dimethyl-5-hydroxypyrrolidine-1,2-dicarboxylate 
• 2133-40-6 L-proline methyl ester monohydrochloride 
• 67-56-1 methanol 
• 74761-41-4 (S)-1-(methoxycarbonyl)pyrrolidine-2-carboxylic acid 
• 83487-05-2 (5S)-N-(methoxycarbonyl)-5-(methoxycarbonyl)-2-pyrroline 

Downstream Products

• 113089-16-0 (S)-2-Formyl-pyrrolidine-1-carboxylic acid methyl ester 
• 618387-12-5 1-methoxycarbonyl-2-hydroxymethylpyrrolidine 
• 129446-24-8 (2R-trans)-2-butyl-5-heptyl-1-phenylsulfonylpyrrolidine 
• 129446-23-7 (2R,5R)-5-Butyl-2-heptylpyrrolidine 
• 134354-01-1 3,3,3-Trifluoro-1-((2R,5R)-2-heptyl-5-hex-5-enyl-pyrrolidin-1-yl)-2-methoxy-2-phenyl-propan-1-one 
• 134353-98-3 (2R,5S)-2-Heptyl-5-(toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid methyl ester 
• 134452-61-2 (2R,5R)-5-Ethyl-2-heptyl-1-phenylsulfonylpyrrolidine 
• 93272-16-3 5-benzyloxy-N_b-methoxycarbonyl-L-tryptophan 
• 89434-13-9 5-benzyloxy-N_b-methoxycarbonyl-L-tryptophan methyl ester 
• 93299-38-8 5-bromo-L-tryptophan methyl ester 
• 2504-22-5 5-methoxy-L-tryptophan 
• 6548-09-0 5-bromo-L-tryptophan 
• 154-07-4 5-chloro-L-tryptophan 
• 56-69-9 5-hydroxy-L-tryptophan 

Relevant articles and documents

Design and stereoselective synthesis of ProM-2: A spirocyclic diproline mimetic with polyproline type II (PPII) helix conformation

With the aim of developing polyproline type II helix (PPII) secondary-structure mimetics for the modulation of prolin-rich-mediated protein-protein interactions, the novel diproline mimetic ProM-2 was designed by bridging the two pyrrolidine rings of a diproline (Pro-Pro) unit through a Z-vinylidene moiety. This scaffold, which closely resembles a section of a PPII helix, was then stereoselectively synthesized by exploiting a ruthenium-catalyzed ring-closing metathesis (RCM) as a late key step. The required vinylproline building blocks, that is, (R)-N-Boc-2-vinylproline (Boc=tert-butyloxycarbonyl) and (S,S)-5-vinylproline-tert-butyl ester, were prepared on a gram scale as pure stereoisomers. The difficult peptide coupling of the sterically demanding building blocks was achieved in good yield and without epimerization by using 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU)/N,N-diisopropylethylamine (DIPEA). The RCM proceeded smoothly in the presence of the Grubbs II catalyst. Stereostructural assignments for several intermediates were secured by X-ray crystallography. As a proof of concept, it was shown that certain peptides containing ProM-2 exhibited improved (canonical) binding towards the Ena/VASP homology 1 (EVH1) domain as a relevant protein interaction target.

Exercises in pyrrolidine chemistry: Gram scale synthesis of a Pro-Pro dipeptide mimetic with a polyproline type II helix conformation

A practical and scalable synthesis of a Fmoc-protected tricyclic dipeptide mimetic (6), that is, a 1,4-diaza-tricyclo-[8.3.03, 7]-tridec-8-ene derivative resembling a rigidified di-L-proline in a polyproline type II (PPII) helix conformation, was developed. The strategy is based on a Ru-catalyzed ring-closing metathesis of a dipeptide (4) prepared by PyBOP coupling of cis-5-vinylproline tert-butylester (2) and trans-N-Boc-3-vinylproline (rac-3) followed by chromatographic diastereomer separation. Building block 2 was prepared from L-proline in six steps via electrochemical C5-methoxylation, cyanation and conversion of the nitrile into a vinyl substituent. Building block rac-3 was prepared in five steps exploiting a Cu-catalyzed 1,4-addition of vinyl-MgBr to a 2,3-dehydroproline derivative in the key step. In the course of the investigation subtle dependencies of protecting groups on the reactivity of the 2,3- and 2,5-disubstituted pyrrolidine derivatives were observed. The configuration and conformational preference of several intermediates were determined by X-ray crystallography. The developed synthesis allows the preparation of substantial amounts of 6, which will be used in the search for new small molecules for the modulation of protein-protein interactions involving prolin-rich motifs (PRDs).

Efficient and Expeditious Protocols for the Synthesis of Racemic and Enantiomerically Pure Endocyclic Enecarbamates from N-Acyl Lactams and N-Acyl Pyrrolidines

A mild, practical, and straightforward protocol for the construction of endocyclic enecarbamates starting from N-acyl lactams and N-acyl pyrrolidines is presented. Lactams were reduced to the corresponding α-hydroxycarbamates in good to excellent yields using DIBAL-H, SuperHydride, or NaBH4 followed by β-elimination (dehydration) promoted by trifluoroacetic anhydride in the presence of hindered nitrogenated bases such as 2,6-lutidine, diisopropylethylamine, or triethylamine. Small variations of this protocol permitted the preparation of several endocyclic enecarbamates (12 examples) in good to excellent overall yields (56-96%). The protocol was demonstrated to be applicable to several ring sizes, compatible with different protecting groups, and to be mild enough to prevent racemization of racemization-prone stereocenters. The efficacy of the procedure in the preparation of enantiomerically pure endocyclic enecarbamates was also demonstrated and compared to the commonly used Shono's protocol, which in our hands led to partial racemization of the endocyclic enecarbamate 18c.