64982-61-2

Usage

Uses

Used in Pharmaceutical Research and Development:
(S)-1-Methyl-1,2,3,4-tetrahydro-isoquinoline is utilized as a research compound for its potential role as a dopamine receptor antagonist, which is significant in the study and treatment of neurological disorders. Its interaction with the central nervous system makes it a valuable candidate for drug development.
Used in Neurological Disorders Research:
(S)-1-Methyl-1,2,3,4-tetrahydro-isoquinoline is used as a research tool to investigate its potential neuroprotective and antioxidant effects, which are crucial for the development of novel drugs targeting neurological disorders. Its ability to protect neurons and reduce oxidative stress could lead to breakthroughs in treating conditions such as Parkinson's disease and other neurodegenerative diseases.

Upstream product

• 102922-31-6 (R)-2-((S)-4-Isopropyl-4,5-dihydro-oxazol-2-yl)-1-methyl-1,2,3,4-tetrahydro-isoquinoline 
• 4965-09-7 1-methyl-1,2,3,4-tetrahydroisoquinoline 
• 487-68-3 mesytaldehyde 
• 1346681-71-7 (1E)-4-hydroxy-1-mesityl-4-methylpent-1-en-3-one 

Downstream Products

• 1721-93-3 1-methylisoquinoline 
• 4965-09-7 1-methyl-1,2,3,4-tetrahydroisoquinoline 
• 178307-42-1 Revaprazan hydrochloride 
• 1346681-97-7 benzyl (1R)-1-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate 

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.