869884-00-4

Basic information

• Product Name: (S)-1,2,3,4-tetrahydro-1-phenylisoquinoline D-(-)-tartrate
• Synonyms: (S)-1,2,3,4-tetrahydro-1-phenylisoquinoline D-(-)-tartrate;Isoquinoline,1,2,3,4-tetrahydro-1-phenyl-(1s),;(S)-1,2,3,4-Tetrahydro-1-phenylisoquinoline (2S,3S)-2,3-dihydroxybutanedioate;(S)-1,2,3,4-tetrahyd;(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (2S,3S)-2,3-dihydroxysuccinate;(S)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline tartrate;SZEOPQAHUUEDMC-XQIJAYBJSA-N
• CAS NO: 869884-00-4
• Molecular Formula: C₄H₆O₆*C₁₅H₁₅N
• Molecular Weight: 359.37
• Mol File: 869884-00-4.mol

Chemical Properties

• Boiling Point: 338.4 °C at 760 mmHg
• Flash Point: 166.9 °C
• Appearance: /
• Vapor Pressure: 9.87E-05mmHg at 25°C
• CAS DataBase Reference: (S)-1,2,3,4-tetrahydro-1-phenylisoquinoline D-(-)-tartrate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1,2,3,4-tetrahydro-1-phenylisoquinoline D-(-)-tartrate(869884-00-4)
• EPA Substance Registry System: (S)-1,2,3,4-tetrahydro-1-phenylisoquinoline D-(-)-tartrate(869884-00-4)

Safety Data

• Hazardous Substances Data: 869884-00-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-1,2,3,4-Tetrahydro-1-phenylisoquinoline D-(-)-tartrate is used as a key component in the development of new therapeutic drugs. Its chiral nature allows for the creation of enantiomer-specific medications, which can have different effects on the body and may lead to more targeted and effective treatments.
Used in Research and Development:
(S)-1,2,3,4-Tetrahydro-1-phenylisoquinoline D-(-)-tartrate is utilized in research and development for the discovery and synthesis of new chemical compounds. Its unique structure and properties make it a valuable tool for scientists to explore and understand the behavior of chiral molecules in various chemical reactions and processes.
Used in Chemical Synthesis Processes:
(S)-1,2,3,4-Tetrahydro-1-phenylisoquinoline D-(-)-tartrate is employed as a reactant or intermediate in chemical synthesis processes. Its versatility and reactivity in various chemical reactions contribute to the creation of new compounds with potential applications in various industries, including pharmaceuticals, materials science, and more.

InChI:InChI=1/C15H15N.C4H6O6/c1-2-7-13(8-3-1)15-14-9-5-4-6-12(14)10-11-16-15;5-1(3(7)8)2(6)4(9)10/h1-9,15-16H,10-11H2;1-2,5-6H,(H,7,8)(H,9,10)/t15-;1-,2-/m00/s1

Upstream product

• 1007222-24-3 1-phenyl-1,2,3,4-tetrahydroisoquinoline oxalate 
• 147-71-7 D-tartaric acid 
• 52250-50-7 1-phenyl-3,4-dihydroisoquinoline 
• 3278-14-6 N-phenethylbenzamide 
• 98-88-4 benzoyl chloride 
• 64-04-0 phenethylamine 
• 22990-19-8 1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 17507-05-0 1-phenyl-1,4-dihydro-3(2H)-isoquinolinone 

Downstream Products

• 1195949-26-8 (S)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carbonyl chloride 
• 22990-19-8 (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 242478-37-1 solifenacin 
• 1262506-09-1 solifenacin succinate 

Relevant articles and documents

Preparation method for (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

The invention relates to a medical intermediate, in particular to a preparation method for (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline. Benzoyl chloride or benzoic acid, phenylethylamine, alkali metalhydroxide and water are mixed to react, N-(2-phenethyl)benzamide, phosphorus pentoxide and phosphorus chloride at a certain ratio are mixed and heated with organic solvent, obtained 1-phenyl-3,4-dihydroisoquinoline, a first alcohol solvent and borohydride are mixed to react, the obtained 1-phenyl-1,2,3,4-dihydroisoquinoline, a second alcohol solvent, water and D-tartaric acid are mixed and heatedto react, the obtained (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline tartrate, alkali metal hydroxide and water are mixed to obtain a target product. The preparation method for (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline has the advantages of simpleness in operation and aftertreatment.

Solifenacin succinate raw medicine synthesis process

The invention discloses a solifenacin succinate raw medicine synthesis process. 2-phenylethylamine and 3-quinuclidinone hydrochloride are respectively used as starting raw materials for synthesizing afragment A and a fragment B; then, condensation reaction occurs to generate solifenacin; through salt formation, the solifenacin succinate is obtained. The process is characterized in that straight-chain paraffin and water are used as reaction solvents; alkali metal hydroxides or carbonate and bicarbonates of the alkali metal hydroxides are used as acid-binding agents; phenylethylamine and benzoyl chloride take acylation reaction to generate midbodies 1 of solid precipitation fragments A insoluble in reaction solvents; in the post treatment process, filtering is directly performed; isomers ofthe fragment A are subjected to catalytic racemization through alkali metal hydroxides by using dimethylsulfoxide as a solvent, so that the byproduct isomers can be recovered and utilized; in the second-step reaction post treatment of the fragment B, a conventional pressure reduced distillation method is used for obtaining high-purity and high-yield 3-acetoxyquinine acetate. The invention provides a novel synthesis process with the advantages of high yield and economic and environment-friendly effects, and is suitable for industrial mass production.

1-phenyl -1, 2, 3, 4-isoquinoline method for the preparation of

The invention provides a 1-phenyl-1, 2, 3, 4-tetrahydroisoquinoline preparation method. The 1-phenyl-1, 2, 3, 4-tetrahydroisoquinoline preparation method comprises the following steps of: mixing benzoyl chloride or benzoic acid, phenethylamine and alkali metal hydroxide with water, and reacting to obtain N-(2-phenethyl) benzamide; then mixing the N-(2-phenethyl) benzamide with phosphorus pentoxide, chloride phosphorus and a benzene solvent, heating and reacting to obtain 1-phenyl-3, 4-dihydro-isoquinoline; and further mixing the 1-phenyl-3, 4-dihydro-isoquinoline with a first alcohol solvent and hydroboron, and reacting to obtain the product. Compared with the prior art, the 1-phenyl-1, 2, 3, 4-tetrahydroisoquinoline preparation method has the advantages that firstly, no organic solvents are added, the product N-(2-phenethyl) benzamide is insoluble in an aqueous solution, and therefore, the steps of skimming and the like are avoided in the after-treatment process, and the after-treatment operation is simplified; secondarily, as the organic solvents are not added, the cost is reduced, and the pollution to environments is avoided; and thirdly, as the phosphorus pentoxide and the chloride phosphorus are subjected to oxidization cyclization reaction, polyphosphoric acids are prevented from being heated and decomposed to generate hypertoxic phosphorus oxide exhaust gas.

Engineering an enantioselective amine oxidase for the synthesis of pharmaceutical building blocks and alkaloid natural products

The development of cost-effective and sustainable catalytic methods for the production of enantiomerically pure chiral amines is a key challenge facing the pharmaceutical and fine chemical industries. This challenge is highlighted by the estimate that 40-45% of drug candidates contain a chiral amine, fueling a demand for broadly applicable synthetic methods that deliver target structures in high yield and enantiomeric excess. Herein we describe the development and application of a "toolbox" of monoamine oxidase variants from Aspergillus niger (MAO-N) which display remarkable substrate scope and tolerance for sterically demanding motifs, including a new variant, which exhibits high activity and enantioselectivity toward substrates containing the aminodiphenylmethane (benzhydrylamine) template. By combining rational structure-guided engineering with high-throughput screening, it has been possible to expand the substrate scope of MAO-N to accommodate amine substrates containing bulky aryl substituents. These engineered MAO-N biocatalysts have been applied in deracemization reactions for the efficient asymmetric synthesis of the generic active pharmaceutical ingredients Solifenacin and Levocetirizine as well as the natural products (R)-coniine, (R)-eleagnine, and (R)-leptaflorine. We also report a novel MAO-N mediated asymmetric oxidative Pictet-Spengler approach to the synthesis of (R)-harmicine.

Processes for optical resolution of 1-phenyl-1,2,3,4-tetrahydroisoquinoline

Optically pure 1(S)-phenyl-1,2,3,4-tetrahydroisoquinoline tartrate is prepared. The 1(S)-phenyl-1,2,3,4-tetrahydroisoquinoline tartrate is particularly useful for preparing solifenacin succinate.