27854-93-9

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
(S)-1-Pyridin-3-yl-ethylamine 2HCl is used as a key intermediate in the synthesis of new therapeutic agents for various medical conditions. Its unique structure and properties allow it to interact with specific biological targets, making it a valuable component in the development of novel drugs.
Used in the Synthesis of Biologically Active Compounds:
In the field of medicinal chemistry, (S)-1-Pyridin-3-yl-ethylamine 2HCl is employed as a building block for the creation of biologically active compounds. Its ability to form various chemical bonds and its compatibility with different molecular structures contribute to the design and synthesis of potential drug candidates.
Used in the Study of Biological Systems:
(S)-1-Pyridin-3-yl-ethylamine 2HCl is utilized in research to investigate its effects on biological systems. By examining its interactions with different cellular components and pathways, scientists can gain insights into its potential therapeutic applications and mechanisms of action.
Used in the Development of Drug Delivery Systems:
The hydrochloride salt form of (S)-1-Pyridin-3-yl-ethylamine 2HCl enhances its solubility, making it suitable for use in drug delivery systems. This property allows for the development of formulations that can effectively deliver the compound to target sites within the body, improving its therapeutic efficacy and reducing potential side effects.

Upstream product

• 926921-86-0 (R_S)-N-[1-(pyridin-3-yl)ethylidene]-2-methylpropane-2-sulfinamide 
• 1010079-98-7 (E)-1-(pyridin-3-yl)ethanone O-benzyl oxime 
• 350-03-8 methyl-3-pyridylketone 
• 500-22-1 3-pyridinecarboxaldehyde 
• 220315-22-0 (R)-(-)-N-(3-pyridylmethylidene)-2-methylpropane-2-sulfinamide 
• 1013624-59-3 (R)-2-methyl-N-(1-(pyridin-3-yl)ethyl)propane-2-sulfinamide 
• 106881-77-0 (E)-1-(pyridin-3-yl)ethanone oxime 
• 56129-55-6 1-pyridin-3-yl-ethylamine 

Downstream Products

• 40154-84-5 (S)-1-(pyridin-3-yl)ethan-1-amine hydrochloride 

Relevant academic research and scientific papers

Stereospecific Intramolecular Arylation of 2- and 3-Pyridyl Substituted Alkylamines via Configurationally Stable α-Pyridyl Organolithiums

Treatment of N′-aryl urea derivatives of enantiomerically enriched α-(2-pyridyl) and α-(3-pyridyl)alkylamines with a base leads to the migration of the N′-aryl substituent from N to C in a nonclassical' intramolecular nucleophilic aromatic substitution re

Asymmetric Biocatalytic Synthesis of Fluorinated Pyridines through Transesterification or Transamination: Computational Insights into the Reactivity of Transaminases

The synthesis of a family of pyridines bearing a fluorinated substituent on the aromatic ring has been carried out through two independent and highly stereoselective chemoenzymatic strategies. Short chemical synthetic routes toward fluorinated racemic amines and prochiral ketones have been developed, which served as substrates to explore the suitability of lipases and transaminases in asymmetric biotransformations. The lipase-catalyzed kinetic resolution via acylation of racemic amines proceeded smoothly giving conversions close to 50% and excellent enantioselectivities. Alternatively, the biotransamination of the corresponding prochiral ketones was investigated giving access to both optically pure amine enantiomers using transaminases with complementary selectivity. High to quantitative conversion values were achieved, which allowed the isolation of the amines in moderate to high yields (40–88%). A deeper understanding of the latter process was enabled by performing theoretical calculations on thermodynamic and mechanistic aspects. Calculations showed that the biotransamination reactions are highly favoured by the presence of fluorine atoms and the pyridine ring. (Figure presented.).

Asymmetric Biocatalytic Amination of Ketones at the Expense of NH3 and Molecular Hydrogen

A biocatalytic system is presented for the stereoselective amination of ketones at the expense of NH3 and molecular hydrogen. By using a NAD+-reducing hydrogenase, an alanine dehydrogenase, and a suitable ω-transaminase, the R- as well as the S-enantiomer of various amines could be prepared with up to >99% ee and 98% conversion. (Chemical Equation Presented).

Transaminases applied to the synthesis of high added-value enantiopure amines

Critical parameters affecting the stereoselective amination of (hetero)aromatic ketones using transaminases have been studied, such as temperature, pH, substrate concentration, cosolvent, and source and percentage of amino donor, to further optimize the production of enantiopure amines using both (S)- and (R)-selective biocatalysts from commercial suppliers. Interesting enantiopure amino building blocks have been obtained, overcoming some limitations of traditional chemical synthetic methods. Representative processes were scaled up, affording halogenated and heteroaromatic amines in enantiomerically pure form and good isolated yields.

Efficient kinetic resolution of racemic amines using a transaminase in combination with an amino acid oxidase

A range of enantiomerically pure (R)- and (S)-configured chiral amines has been prepared in excellent e.e. (99%) by combining a transaminase enzyme with an amino acid oxidase and catalytic quantities of pyruvate.

CATALYTIC ASYMMETRIC SYNTHESIS OF PRIMARY AMINES VIA BORANE REDUCTION OF OXIME ETHERS USING SPIROBORATE ESTERS

Asymmetric reduction of arylalkyl and pyridylalkyl ketoxime ether with borane catalyzed by several chiral spiroborates derived from non-racemic 1,2-amino alcohols are presented. Complete conversion of oxime to primary amine is highly dependant of the catalyst, source and amount of borane and temperature. The conversion and enantioselectivity is determined by the benzylic substitution of the oxime. After optimization, a catalyst derived from diphenyl valinol could, successfully, afford primary amines with good yield and enantioselectivity up to 99% ee. Using the developed methodology, other related non-racemic primary pyridyl alkyl methanamines were also prepared in high chemical yield and excellent enantioselectivity.

An easy route to optically active 1-substituted-1-pyridyl-methylamines by diastereoselective reduction of enantiopure N-tert-butanesulfinyl ketimines

The reduction of enantiopure N-tert-butanesulfinyl ketimines derived from pyridyl ketones afforded the related N-tert-butanesulfinyl amines with high yields and diastereoselectivities.