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Usage

Uses

Used in Pharmaceutical Industry:
(R)-1-Methyl-1,2,3,4-tetrahydroisoquinoline is used as a potential therapeutic agent for its neuroprotective and anti-inflammatory properties, targeting various neurological and psychiatric conditions.
Used in Neurodegenerative Disease Treatment:
(R)-1-Methyl-1,2,3,4-tetrahydroisoquinoline is used as a potential treatment for neurodegenerative diseases such as Parkinson's disease, due to its demonstrated biological activity in the central nervous system and its interaction with dopamine receptors.
Used in Research and Development:
(R)-1-Methyl-1,2,3,4-tetrahydroisoquinoline is used as a subject of study in research and development for understanding its pharmacological properties and potential applications in the treatment of various neurological and psychiatric conditions.

Upstream product

• 4965-09-7 1-methyl-1,2,3,4-tetrahydroisoquinoline 
• 1346681-71-7 (1E)-4-hydroxy-1-mesityl-4-methylpent-1-en-3-one 
• 102922-31-6 (R)-2-((S)-4-Isopropyl-4,5-dihydro-oxazol-2-yl)-1-methyl-1,2,3,4-tetrahydro-isoquinoline 

Relevant academic research and scientific papers

Acylative kinetic resolution of racemic methyl-substituted cyclic alkylamines with 2,5-dioxopyrrolidin-1-yl (: R)-2-phenoxypropanoate

The diastereoselective acylation of a number of racemic methyl-substituted cyclic alkylamines with active esters of 2-phenoxypropanoic acid was studied in detail. The ester of (R)-2-phenoxypropanoic acid and N-hydroxysuccinimide was found to be the most selective agent. The highest stereoselectivity was observed in the kinetic resolution of racemic 2-methylpiperidine in toluene at -40 °C (selectivity factor s = 73) with the predominant formation of (R,R)-amide (93.7% de). To explain the observed stereoselectivity, DFT modelling of the transition states in the reactions of the title acylating agent with 2-methylpiperidine and 2-methylpyrrolidine was performed. The calculated values were in good agreement with experimental data. It has been demonstrated that the acylation proceeds via a concerted mechanism, in which the addition of an amine occurs simultaneously with the elimination of the hydroxysuccinimide fragment. The high stereoselectivity of the (R,R)-amide formation is largely ensured by the lower steric hindrances in the transition states as compared to the formation of (R,S)-amide.

Catalytic kinetic resolution of cyclic secondary amines

The catalytic resolution of racemic cyclic amines has been achieved by an enantioselective amidation reaction featuring an achiral N-heterocyclic carbene catalyst and a new chiral hydroxamic acid cocatalyst working in concert. The reactions proceed at room temperature, do not generate nonvolatile byproducts, and provide enantioenriched amines by aqueous extraction.

Chiral Dipole-Stabilized Anions: Experiment and Theory in Benzylic and Allylic Systems. Stereoselective Deprotonations, Pyramidal Inversions, and Stereoselective Alkylations of Lithiated (Tetrahydroisoquinolyl)oxazolines

The stereoselective alkylation of chiral (tetrahydroisoquinolyl)oxazolines has been investigated.We report the details of this investigation, including an examination of the effect of both temperature and oxazoline substituent structure on the alkylation diastereoselectivity, a comparison of monodentate vs bidentate chelation of the organolithium, an evaluation of the effect of solvent and chelating solvent additives, the regiochemistry of alkylation of (3,4-dehydropiperidino)oxazolines, lithiation-alkylation experiments on stereoselectively deuterated monodentate and bidentate isoquinolinolyloxazolines, and semiempirical molecular orbital calculations on the organolithium diastereomers 13a,b.There are two distinct stereoselective processes involved in the overall transformation. the proposed mechanism includes an oxazoline-alkyllithium coordination complex that controls the selectivity of the deprotonation step, whereas the selectivity of the electrophilic quench is governed by effects that are as yet undetermined.