92053-25-3

Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-2-(1-HYDROXY-1-METHYLETHYL) PYRROLIDINE is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and reactivity allow for the development of new drugs with improved efficacy and selectivity.
Used in Agrochemical Synthesis:
In the agrochemical industry, (S)-2-(1-HYDROXY-1-METHYLETHYL) PYRROLIDINE serves as a crucial building block for the creation of novel agrochemicals. Its incorporation into these compounds can lead to enhanced crop protection and yield.
Used in Asymmetric Catalysis:
(S)-2-(1-HYDROXY-1-METHYLETHYL) PYRROLIDINE may be employed as a chiral catalyst in asymmetric catalysis, a field that focuses on the selective synthesis of enantiomerically pure compounds. Its chiral nature can be leveraged to control the stereochemistry of reactions, leading to the production of enantiomerically enriched products.
Used as a Chiral Auxiliary in Organic Synthesis:
In organic synthesis, (S)-2-(1-HYDROXY-1-METHYLETHYL) PYRROLIDINE can be utilized as a chiral auxiliary. Chiral auxiliaries are non-reactive components that are temporarily attached to a substrate to control the stereochemistry of a reaction. The presence of this chiral molecule can guide the reaction to produce a specific enantiomer, which is particularly important in the synthesis of biologically active compounds.
Overall, (S)-2-(1-HYDROXY-1-METHYLETHYL) PYRROLIDINE is a versatile and valuable chemical compound with a wide range of applications in various industries, including pharmaceuticals, agrochemicals, and organic synthesis. Its unique structure and reactivity, along with its potential in asymmetric catalysis and as a chiral auxiliary, make it a promising candidate for further research and development.

Upstream product

• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 75-16-1 methylmagnesium bromide 
• 59936-29-7 (S)-N-(tert-butoxycarbonyl)proline methyl ester 
• 77581-28-3 (S)-proline-N-ethyl carbamate methyl ester 
• 74-88-4 methyl iodide 
• 147-85-3 L-proline 
• 672324-99-1 C₂HF₃O₂*C₇H₁₅NO 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 5211-23-4 N-carbobenzyloxy-L-proline methyl ester 
• 113304-84-0 N-benzyl-(S)-proline methyl ester 
• 118970-92-6 (S)-(-)-1-benzyl-2-(1-hydroxy-1-methylethyl)-pyrrolidine 
• 51207-68-2 (2S)-N-Benzyloxycarbony-2-(1'-hydroxy-1'-methylethyl)pyrrolidine 

Relevant academic research and scientific papers

Isosteric expansion of the structural diversity of chiral ligands: Design and application of proline-based N,N′-dioxide ligands for copper-catalyzed enantioselective Henry reactions

Chiral N,N′-dioxide catalysts were designed based on isosteric approach. Using L-Proline as the starting material, a variety of chiral N,N′-dioxide ligands were obtained via conventional functional group transformations and were utilized in asymmetric Henry reactions between nitromethane and aromatic aldehydes. Using the N,N′-dioxide-copper(II) complexes as the catalysts, asymmetric Henry reaction produced the corresponding β-nitroalcohols in up to 66% yields and up to 83% ee's under mild conditions. The reactions were easy to carry out, and special care such as air or moisture-free conditions was not required.

COMPOUNDS, COMPOSITIONS AND METHODS FOR SYNTHESIS

The present disclosure, among other things, provides technologies for synthesis, including reagents and methods for stereoselective synthesis. In some embodiments, the present disclosure provides compounds useful as chiral auxiliaries. In some embodiments, the present disclosure provides reagents and methods for oligonucleotide synthesis. In some embodiments, the present disclosure provides reagents and methods for chirally controlled preparation of oligonucleotides. In some embodiments, technologies of the present disclosure are particularly useful for constructing challenging internucleotidic linkages, providing high yields and stereoselectivity.

Mechanistic investigations of the asymmetric hydrosilylation of ketimines with trichlorosilane reveals a dual activation model and an organocatalyst with enhanced efficiency

Structural probes used to help elucidate mechanistic information of the organocatalyzed asymmetric ketimine hydrosilylation have revealed a new catalyst with unprecedented catalytic activity, maintaining adequate performance at 0.01 mol% loading. A new ‘dual activation’ model has been proposed that relies on the presence of both a Lewis basic and Br?nsted acidic site within the catalyst architecture.

Iminium Catalysis inside a Self-Assembled Supramolecular Capsule: Modulation of Enantiomeric Excess

The noncovalent combination of a supramolecular host with iminium organocatalysis is described. Due to cation–π interactions the reactive iminium species is held inside the host and reacts in this confined environment. The products formed differ up to 92 % ee from the control experiments without added host. A model rationalizing the observed difference is presented.

IDO INHIBITORS

There are disclosed compounds that modulate or inhibit the enzymatic activity of indoleamine 2,3-dioxygenase (IDO), pharmaceutical compositions containing said compounds and methods of treating proliferative disorders, such as cancer, viral infections and/or inflammatory disorders utilizing the compounds of the invention.

Highly Enantioselective Epoxidation of α,β-Unsaturated Ketones Catalyzed by Rare-Earth Amides [(Me3Si)2N]3RE(μ-Cl)Li(THF)3 with Phenoxy-Functionalized Chiral Prolinols

A simple and efficient catalytic enantioselective epoxidation of α,β-unsaturated ketones has been successfully developed, which was catalyzed by rare-earth metal amides [(Me3Si)2N]3RE(μ-Cl)Li(THF)3 (RE = Yb (1), La (2), Sm (3), Y (4), Lu (5)) in the presence of phenoxy-functionalized chiral prolinols at room temperature using tert-butylhydroperoxide (TBHP) as the oxidant. The combination of an Yb-based amide 1 and a chiral proligand (S)-2,4-di-tert-butyl-6-((2-(hydroxydiphenylmethyl)pyrrolidin-1-yl)methyl)phenol) performed very well, and both the yields and the enantiomeric excess of the chiral epoxides reached up to 99% and 99% ee. (Figure Presented).

Asymmetric hydroamination catalyzed by a new chiral zirconium system: Reaction scope and mechanism

A new class of chiral zirconium complexes supported by chiral tridentate [O-NO-]-type of ligands derived from amino acids were synthesized and structurally characterized. They catalyzed asymmetric hydroamination/cyclization of primar

PYRAZINE COMPOUNDS AS PHOSPHODIESTERASE 10 INHIBITORS

Pyrazine compounds, and compositions containing them, and processes for preparing such compounds. Provided herein also are methods of treating disorders or diseases treatable by inhibition of PDE10, such as obesity, non-insulin dependent diabetes, schizophrenia, bipolar disorder, obsessive-compulsive disorder, and the like.

Water-compatible iminium activation: Organocatalytic Michael reactions of carbon-centered nucleophiles with enals

(Chemical Equation Presented) A pool of water-compatible catalysts, namely the chiral prolinol-based catalysts 1, has been developed for highly enantioselective C-C bond-forming Michael reactions in water (see scheme). The synthesis of (S)-Rolipram, a type IV phosphodiesterase inhibitor, was also demonstrated.

PYRAZOLOPYRIMIDINES AS CYCLIN-DEPENDENT KINASE INHIBITORS

In its many embodiments, the present invention provides a novel class of pyrazolo[1,5-a]pyrimidine compounds as inhibitors of cyclin dependent kinases, methods of preparing such compounds, pharmaceutical compositions containing one or more such compounds, methods of preparing pharmaceutical formulations comprising one or more such compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with the CDKs using such compounds or pharmaceutical compositions.