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

Description

(S)-DiMethyl pyrrolidine-1,2-dicarboxylate, commonly known as piracetam, is a synthetic compound belonging to the racetam class of drugs. It is a derivative of the neurotransmitter GABA and is recognized for its potential to enhance cognitive function by modulating the activity of neurotransmitters in the brain. Piracetam has been extensively studied for its ability to improve memory, learning, and overall cognitive function, making it a promising candidate for various applications in the medical and pharmaceutical fields.

Uses

Used in Pharmaceutical Industry:
(S)-DiMethyl pyrrolidine-1,2-dicarboxylate is used as a cognitive enhancer for its ability to improve memory, learning, and overall cognitive function. It is particularly beneficial for individuals seeking to enhance their cognitive performance or for those suffering from cognitive decline.
Used in Treatment of Cognitive Disorders:
In the medical field, (S)-DiMethyl pyrrolidine-1,2-dicarboxylate is used as a therapeutic agent for the treatment of cognitive disorders such as dementia and stroke. Its neuroprotective effects make it a valuable asset in managing and alleviating the symptoms associated with these conditions.
Used in Dyslexia and ADHD Management:
(S)-DiMethyl pyrrolidine-1,2-dicarboxylate is also used as a potential treatment for conditions like dyslexia and ADHD. Its ability to modulate neurotransmitter activity in the brain has shown promise in improving symptoms and overall cognitive function in individuals with these conditions.

Upstream product

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

Downstream Products

• 113089-16-0 (S)-2-Formyl-pyrrolidine-1-carboxylic acid methyl ester 
• 618387-12-5 1-methoxycarbonyl-2-hydroxymethylpyrrolidine 
• 185385-14-2 cis-5-phenylsulfanyl-pyrrolidine-1,2-dicarboxylic acid dimethyl ester 
• 185385-15-3 trans-5-phenylsulfanyl-pyrrolidine-1,2-dicarboxylic acid dimethyl ester 
• 160033-52-3 (2S,5R)-5-methyl-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 83487-05-2 N-carbomethoxy-4,5-dehydroproline methyl ester 
• 154-06-3 2-Amino-3-(5-methyl-1H-indol-3-yl)-propionic acid 
• 56-69-9 5-hydroxy-L-tryptophan 
• 154-07-4 5-chloro-L-tryptophan 
• 6548-09-0 5-bromo-L-tryptophan 
• 2504-22-5 5-methoxy-L-tryptophan 
• 93299-38-8 5-bromo-L-tryptophan methyl ester 
• 89434-13-9 5-benzyloxy-N_b-methoxycarbonyl-L-tryptophan methyl ester 
• 93272-16-3 5-benzyloxy-N_b-methoxycarbonyl-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.

Practical one-pot double functionalizations of proline

Solubilization of proline as the triethylammonium salt allows N-protection (as the Boc, Cbz or Moc derivative) and subsequent esterification or amidation of the carboxy terminus to be performed in an efficient one-pot fashion. Based on this concept, highly practical protocols were developed to prepare a series of proline derivatives (including Pro-Ser dipetides, Weinreb amides and N-protected proline esters), which are important intermediates, for instance, for the synthesis of proline-derived peptides, chiral reagents and catalysts for asymmetric synthesis. Georg Thieme Verlag Stuttgart - New York.

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.