19036-73-8

Usage

Uses

Used in Pharmaceutical Industry:
(S)-1-(3-TRIFLUOROMETHYLPHENYL)-2-AMINOPROPANE is used as a potential therapeutic agent for the treatment of various neurological and psychiatric conditions. Its selective dopamine reuptake inhibition property makes it a promising candidate for conditions related to dopamine dysregulation.
Used in Research and Development:
(S)-TFMSPP is used as a research tool in the study of neurotransmitter systems, particularly those involving dopamine. Its ability to selectively inhibit dopamine reuptake allows researchers to investigate the role of dopamine in various physiological and pathological processes.
Used as a Reference Standard:
(S)-1-(3-TRIFLUOROMETHYLPHENYL)-2-AMINOPROPANE is used as a reference standard in analytical studies, particularly in the development and validation of analytical methods for the detection and quantification of related compounds in biological samples or pharmaceutical formulations.

Upstream product

• 213682-62-3 2-[(S)-1-Methyl-2-(3-trifluoromethyl-phenyl)-ethyl]-isoindole-1,3-dione 
• 58225-71-1 (S),(S)-N-(1-phenylethyl)-α-methyl-3-(trifluoromethyl)benzeneethanamine 
• 7440-05-3 palladium 
• 213202-12-1 (S)-N-((S)-1-phenylethyl)-1-(3-(trifluoromethyl)phenyl)propan-2-amine 
• 135561-78-3 (R)-1-(3’-trifluoromethylphenyl)-2-propanol 
• 135561-75-0 1-[(3′-trifluoromethyl)phenyl]-2-propanol 
• 21906-39-8 3-(trifluoromethyl)phenylacetone 

Relevant academic research and scientific papers

METHOD FOR TREATING EPILEPSY

In certain embodiments, the present disclosure is directed to methods and uses for treating a mammal having an epileptic seizure disorder or being at risk for having an epileptic seizure disorder, comprising administering certain herein disclosed isolated fenfluramine enantiomers that are surprisingly effective as anti-epilepsy drugs (AEDs), despite having lower anti-seizure potency than fenfluramine racemate, by virtue of also being less cardiotoxic than fenfluramine racemate. Preferred embodiments contemplate treatment of Dravet syndrome; other preferred embodiments contemplate treatment of other epileptic seizure disorders.

Process for the production of the isomers (R) and (S)-Alpha-methyl-3-(trifluoromethyl)benzeneethanamine

Process for the production of the isomers (R) and (S)-α-methyl-3-(trifluoromethyl)benzeneethanamine, the second being usable as intermediate in the synthesis of the anorexic drug dexfenfluramine (INN), which comprises carrying out a stereospecific reductive amination of 1-(3-trifluoromethyl)phenyl-2-propanone with (R) or (S)-α-methylbenzylamine under hydrogen atmosphere in the presence of a catalyst and in debenzylating the resulting diastereoisomer (R),(R) or (S),(S)-N-(1-phenylethyl)-α-methyl-3-(trifluoromethyl)benzeneethanamine by treatment with hydrogen and catalyst.

Process for the production of the isomers (R) and (S)-α-methyl-3(trifluoromethyl)benzeneethanamine

Process for the production of the isomers (R) and (S)-α-methyl-3-(trifluoromethyl)benzeneethanamine, the second being useful as intermediate in the synthesis of the anorexic drug dexfenfluramine (INN), which comprises carrying out a stereospecific reductive amination of 1-(3-trifluoromethyl)phenyl-2-propanone with (R) or (S)-α-methylbenzylamine under a hydrogen atmosphere in the presence of a catalyst and debenzylating the resulting diastereoisomer (R),(R) or (S),(S)-N-(1-phenylethyl)-α-methyl-3-(trifluoromethyl)benzeneethanamine by treatment with hydrogen and a catalyst.

Homochiral (R)- and (S)-1-heteroaryl- and 1-aryl-2-propanols via microbial redox

Preparation of various heteroaryl propanols 2a-g and of the corresponding propanones 3a-g as starting materials for microbial redox is described. The kinetic resolution of the racemic propanols 2a-g is obtained via oxidation with Pseudomonas paucimobilis and Bacillus stearothermophilus [(R)-alcohols, ee 74-100%]. Similar results are achieved with 3-(2- hydroxypropyl)trifluoromethylbenzene 7 (44%, ee 100% of the (R)-alcohol 6). The reduction of the propanones 3a-d and 3g with baker's yeast and other fungi gives the (S)-alcohols (ee 100%). The pure (S)-alcohols are also obtained by reduction of 1-[3-(trifluoromethyl)phenyl]-2-propanone 7. 1- [(4,4-Dimethyl)-2-(Δ2)oxazolinyl]-2-propanone 3e and 1[2-(Δ2)- thiazolinyl)-2-propanone 3f are not reduced. The heterocyclic rings of (S)- 5-(2-hydroxypropyl)-3-methylisoxazole 2d and of (S)-2-(2-hydroxypropyl)-4- methylthiazole 2g are deblocked to the homochiral enamino ketone 8 (78%) and to the protected β-hydroxy aldehyde 9 (73%), respectively. The (R)-3-(2- hydroxypropyl)trifluoromethylbenzene 6 is transformed into the homochiral precursor of (S)-fenfluramine 10 (overall yield 65%).