64778-78-5

Usage

Uses

Used in Pharmaceutical Synthesis:
(R)-1-(3,4-DIMETHOXYPHENYL) 2-PROPANAMINE is used as a key intermediate in the synthesis of pharmaceuticals and bioactive compounds. Its chiral nature is particularly beneficial for creating enantiomerically pure products, which are essential for ensuring the desired therapeutic effects and minimizing potential side effects.
Used in Drug Production:
(R)-1-(3,4-DIMETHOXYPHENYL) 2-PROPANAMINE serves as a precursor in the production of various drugs and biologically active compounds. Its unique structural properties make it a promising candidate for the development of new medications with improved efficacy and safety profiles.
Used in Medical Treatments:
(R)-1-(3,4-DIMETHOXYPHENYL) 2-PROPANAMINE has been investigated for its potential role in the treatment of certain medical conditions. It has shown promise as an anti-inflammatory agent, which could be useful in managing inflammation-related disorders. Additionally, it has been studied for its antifungal properties, indicating potential applications in treating fungal infections.

InChI:InChI=1/C11H17NO2/c1-8(12)6-9-4-5-10(13-2)11(7-9)14-3/h4-5,7-8H,6,12H2,1-3H3/t8-/m1/s1

Upstream product

• 186581-53-3 diazomethane 
• 2410-01-7 (-)(D)-2-<3,4-Dihydroxy-phenyl>-1-methyl-aethylamin 
• 120-26-3 2-(3,4-dimethoxyphenyl)-1-methylethylamine 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 121-33-5 vanillin 
• 93-15-2 1,2-dimethoxy-4-(2-propenyl)benzene 
• 776-99-8 3,4-dimethoxyphenylacetone 
• 97-53-0 4-allylguaiacol 
• 138908-57-3 (S)-2-((tert-butoxycarbonyl)amino)-3-(3,4-dimethoxyphenyl)propyl methanesulfonate 
• 105779-71-3 (S)-(-)-[2-(3,4-dimethoxyphenyl)-1-hydroxymethylethyl]carbamic acid tert-butyl ester 
• 100388-95-2 (R)-3-(3,4-dimethoxy-phenyl)-2-methyl-propionyl chloride 
• 138908-56-2 (S)-(+)-2-tert-butoxycarbonylamino-3-(3,4-dimethoxyphenyl)propionic acid methyl ester 

Downstream Products

• 51-79-6 urethane 
• 94564-16-6 (R)-1-<2-(3,4-Dimethoxyphenyl)-1-methylethyl>pyrimidin-2,4,6(1H,3H,5H)-trion 
• 1446877-09-3 (R)-ethyl 1-(3,4-dimethoxyphenyl)propan-2-ylcarbamate 
• 1446877-11-7 (1S,3R)-1-(3-hydroxybenzyl)-6,7-dimethoxy-2,3-dimethyl-1,2,3,4-tetrahydroisoquinoline 
• 174336-36-8 (R)-N-(3,4-dimethoxybenzyl)-1-(3,4-dimethoxyphenyl)-prop-2-ylamine 
• 138908-40-4 CL 316243 
• 139013-14-2 5-{(R)-2-[(R)-5-(3-Chloro-phenyl)-2-oxo-oxazolidin-3-yl]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid diethyl ester 
• 138908-58-4 [R-(R*,R*)]-5-(3-chlorophenyl)-3-[2-(3,4-dimethoxylphenyl)-1-methyl-ethyl]-oxazolidin-2-one 
• 142796-56-3 (R)-5-(3-Chloro-phenyl)-3-[(R)-2-(3,4-dihydroxy-phenyl)-1-methyl-ethyl]-oxazolidin-2-one 
• 142796-55-2 (R)-1-(3-Chloro-phenyl)-2-[(R)-2-(3,4-dimethoxy-phenyl)-1-methyl-ethylamino]-ethanol 
• 107779-48-6 N-[(R)-2-(3,4-dimethoxy-phenyl)-1-methyl-ethyl]-toluene-4-sulfonamide 

Relevant academic research and scientific papers

Transaminase-mediated synthesis of enantiopure drug-like 1-(3′,4′-disubstituted phenyl)propan-2-amines

Transaminases (TAs) offer an environmentally and economically attractive method for the direct synthesis of pharmaceutically relevant disubstituted 1-phenylpropan-2-amine derivatives starting from prochiral ketones. In this work, we report the application of immobilised whole-cell biocatalysts with (R)-transaminase activity for the synthesis of novel disubstituted 1-phenylpropan-2-amines. After optimisation of the asymmetric synthesis, the (R)-enantiomers could be produced with 88-89% conversion and >99% ee, while the (S)-enantiomers could be selectively obtained as the unreacted fraction of the corresponding racemic amines in kinetic resolution with >48% conversion and >95% ee. This journal is

Stereoselective Synthesis of 1-Arylpropan-2-amines from Allylbenzenes through a Wacker-Tsuji Oxidation-Biotransamination Sequential Process

Herein, a sequential and selective chemoenzymatic approach is described involving the metal-catalysed Wacker-Tsuji oxidation of allylbenzenes followed by the amine transaminase-catalysed biotransamination of the resulting 1-arylpropan-2-ones. Thus, a series of nine optically active 1-arylpropan-2-amines were obtained with good to very high conversions (74–92%) and excellent selectivities (>99% enantiomeric excess) in aqueous medium. The Wacker-Tsuji reaction has been exhaustively optimised searching for compatible conditions with the biotransamination experiments, using palladium(II) complexes as catalysts and iron(III) salts as terminal oxidants in aqueous media. The compatibility of palladium/iron systems for the chemical oxidation with commercially available and made in house amine transaminases was analysed, finding ideal conditions for the development of a general and stereoselective cascade sequence. Depending on the selectivity displayed by selected amine transaminase, it was possible to produce both 1-arylpropan-2-amines enantiomers under mild reaction conditions, compounds that present therapeutic properties or can be employed as synthetic intermediates of chiral drugs from the amphetamine family. (Figure presented.).

Enantiomeric separation of Novel Psychoactive Substances by capillary electrophoresis using (+)-18-crown-6-tetracarboxylic acid as chiral selector

In the recent years, hundreds of Novel Psychoactive Substances (NPS) have entered both the European and the global drug market. These drugs, which are mainly used for recreational matters, have caused serious social problems. Every year, the spectrum of these misused drugs is enlarged by new derivatives, which are produced by modifications of basic structures of already well-known substances. Additionally, a lot of them possess a stereogenic center which leads to 2 enantiomeric forms. The fact that the pharmacological effects and potencies of the enantiomers of these chiral NPS may differ can be assumed from a broad spectrum of active pharmaceutical ingredients. For this reason, analytical method development regarding enantiomeric separation for these classes of substances is of great pharmaceutical and medical interest. The aim of this work was to create an easy-to-prepare chiral capillary electrophoresis method for the enantioseparation of NPS which contains a primary amino group by means of (+)-18-crown-6-tetracarboxylic acid as chiral selector. Novel Psychoactive Substances were purchased at various Internet stores or represent samples seized by Austrian police. The effects of selector concentration, the electrolyte composition, and the addition of organic modifiers to the background electrolyte on enantioseparation were investigated. Under optimized conditions, the use of 20-mM (+)-18-crown-6-tetracarboxylic acid, 10-mM Tris, and 30-mM citric acid buffer at pH 2.10 turned out to be effective. Fifteen of 24 tested NPS were resolved in their enantiomers within 15?minutes. It was found that all NPS were traded as racemic mixtures.

Controlling stereoselectivity by enzymatic and chemical means to access enantiomerically pure (1S,3R)-1-benzyl-2,3-dimethyl-1,2,3,4- tetrahydroisoquinoline derivatives

A chemoenzymatic strategy for the synthesis of enantiomerically pure novel alkaloids (1S,3R)-1-benzyl-2,3-dimethyl-1,2,3,4-tetrahydroisoquinolines is presented. The key steps are the biocatalytic stereoselective reductive amination of substituted 1-phenyl