83015-26-3

Usage

Uses

Used in Pharmaceutical Industry:
(R)-Tomoxetine is used as a compound active at a novel site on receptor-operated calcium channels for the treatment of neurological disorders and diseases. Its unique mechanism of action allows it to modulate calcium channel activity, which can have therapeutic benefits in various neurological conditions.
The specific stereochemistry of (R)-Tomoxetine contributes to its selectivity and potency, making it a valuable asset in the development of targeted therapies for neurological disorders. Its potential applications include the treatment of conditions such as Alzheimer's disease, Parkinson's disease, and other neurodegenerative disorders, as well as various forms of chronic pain and epilepsy.
Furthermore, the chiral nature of (R)-Tomoxetine may also provide insights into the role of stereochemistry in drug design and development, leading to the discovery of new and more effective therapeutic agents. As research continues, (R)-Tomoxetine may pave the way for innovative treatments and improved patient outcomes in the field of neurology.

InChI:InChI=1/C17H21NO/c1-14-8-6-7-11-16(14)19-17(12-13-18-2)15-9-4-3-5-10-15/h3-11,17-18H,12-13H2,1-2H3/t17-/m1/s1

Upstream product

• 95-49-8 2-methylchlorobenzene 
• 115290-81-8 (R)-N-methyl-3-phenyl-3-hydroxypropylamine 
• 115290-79-4 (R)-3-(2-methylphenoxy)-3-phenylprop-1-yl methanesulfonate 
• 74-89-5 methylamine 
• 114446-47-8 -(-)-1-chloro-3-phenyl-3-(2-methylphenoxy)propane 
• 118856-08-9 butyric acid 2-ethoxycarbonyl-1-phenyl-ethyl ester 
• 838841-85-3 (3S) ethyl β-butyryloxy-β-phenyl propionate 
• 5764-85-2 Ethyl 3-hydroxy-3-phenylpropanoate 
• 96854-34-1 (S)-3-phenyl-1,3-propanediol 
• 100-52-7 benzaldehyde 
• 115290-77-2 (1S) 3-phenyl-3-hydroxypropyl methanesulfonate 
• 936-59-4 3-chloropropiophenone 
• 100306-34-1 3-chloro-1-phenylpropanol 
• 132203-26-0 (S)-3-hydroxy-3-phenylpropanenitrile 

Downstream Products

• 1027094-45-6 (R)-atomoxetine oxalate 
• 851086-84-5 S-rivastigmine-atomoxetine 
• 134619-78-6 (-)-N-tert-butoxycarbonyl-N-methyl-3-phenyl-3-(2-methylphenoxy)propanamine 
• 82248-59-7 atomoxetine hydrochloride 

Relevant academic research and scientific papers

Preparation method of cefamoxetine hydrochloride

The invention discloses a preparation method of tamoxidectin hydrochloride, belongs to the technical field of drug synthesis, and uses 3 - chlorine -1 - phenylpropanone as a raw material to undergo a reduction reaction. The synthesis route has the advantages of few reaction steps, mild reaction conditions,3 - simple 2 - operation, cheap -3 - and easily available raw materials, and low production cost 3 - and -1 - R-chloro - N - phenylpropanone is used as a raw material.

Preparation method of N-methyl-3-(2-methylphenoxy)amphetamine

The invention discloses a preparation method of N-methyl-3-(2-methylphenoxy)amphetamine as shown in a formula III. The preparation method comprises the following step: in DMSO, (S)-N-methyl-3-(2-methylphenoxy)amphetamine as shown in a formula II and potassium tert-butoxide are subjected to racemization reaction to obtain the N-methyl-3-(2-methylphenoxy)amphetamine. Chiral N-methyl-3-(2-methylphenoxy)amphetamine is subjected to efficient racemization under mild conditions, no obvious impurities are generated, and the obtained racemization product can be further split to obtain required (R)-atomoxetine, so that the splitting efficiency of atomoxetine is improved.

Preparation method of atomoxetine hydrochloride

The invention belongs to the technical field of medicines, and particularly relates to a preparation method of atomoxetine hydrochloride serving as a medicine for treating attention deficit hyperactivity. According to the invention, commercially available (E)-N-methyl-3-phenyl-2-propylene-1-amine is adopted as a starting material, and addition, substitution and salification are carried out so as to prepare atomoxetine hydrochloride. The preparation method provided by the invention is simple in preparation process, simple and convenient to operate, relatively high in yield and suitable for industrial production, and can provide sufficient bulk drugs for research and development of medicines.

Enantioselective Heck Arylation of Acyclic Alkenol Aryl Ethers: Synthetic Applications and DFT Investigation of the Stereoselectivity

Herein we report the enantioselective Heck-Matsuda arylation of acyclic E and Z-alkenyl aryl ethers. The reactions were carried out under mild conditions affording the enantioenriched benzyl ethers in a regioselective manner, moderate to good yields (up to 73%), and in good to excellent enantiomeric ratios (up to 97:3). The enantioselective Heck-Matsuda arylation has shown a broad scope (25 examples), and some key Heck-Matsuda adducts were further converted into more complex and valuable scaffolds including their synthetic application in the synthesis of (R)-Fluoxetine, (R)-Atomoxetine, and in the synthesis of an enantioenriched benzo[c]chromene. Finally, in silico mechanistic investigations into the reaction's enantioselectivity were performed using density functional theory. (Figure presented.).

Preparation method of atomoxetine

The invention belongs to the technical field of medicines, and particularly relates to a preparation method of atomoxetine hydrochloride serving as a medicine for treating attention deficit hyperactivity. Commercially available 3-(methylamino)-1-phenylacetone is adopted as a starting material, and undergoes asymmetric reduction, substitution and other reactions to prepare the atomoxetine. The invention mainly aims to prepare the atomoxetine by an asymmetric synthesis method and expand a preparation method of the atomoxetine hydrochloride.

Selective Monomethylation of Amines with Methanol as the C1 Source

The N-monomethyl functionality is a common motif in a variety of synthetic and natural compounds. However, facile access to such compounds remains a fundamental challenge in organic synthesis owing to selectivity issues caused by overmethylation. To address this issue, we have developed a method for the selective, catalytic monomethylation of various structurally and functionally diverse amines, including typically problematic primary aliphatic amines, using methanol as the methylating agent, which is a sustainable chemical feedstock. Kinetic control of the aliphatic amine monomethylation was achieved by using a readily available ruthenium catalyst at an adequate temperature under hydrogen pressure. Various substrates including bio-related molecules and pharmaceuticals were selectively monomethylated, demonstrating the general utility of the developed method.

Minimizing Aryloxy Elimination in RhI-Catalyzed Asymmetric Hydrogenation of β-Aryloxyacrylic Acids using a Mixed-Ligand Strategy

The first example of efficient asymmetric hydrogenation of challenging β-aryloxyacrylic acids was realized using a RhI-complex based on the heterocombination of a readily available chiral monodentate secondary phosphine oxide (SPO) and an achiral monodentate phosphine ligand as the catalyst. Excellent enantioselectivities (92->99% ee) were achieved for a wide variety of chiral β-aryloxypropionic acids with minor aryloxy elimination in most cases. The resultant products were readily transformed into biologically active compounds through simple synthetic manipulations.

A method for preparing optically active 3-amino-1-phenylpropanol derivatives as an intermediate and a method for preparing optically active pharmaceutical products using the same

The present invention relates to a method for preparing a 3-amino-1-phenylpropanol derivative having (R) or (S) optical activity with 80% or more of an enantiomeric excess (ee), which includes a step of performing an asymmetric reduction reaction in the presence of a spiroborate ester catalyst and a hydrogen donor. The invention also relates to a method for preparing an optically active pharmaceutical product, which includes a step of preparing a (R)- or (S)-3-amino-1-phenylpropanol derivative, that is an intermediate, by using the catalyst.(AA) 3-amino-1-phenylpropanol(BB) Tomoxetine(CC) Nisoxetine(DD) FluoxetineCOPYRIGHT KIPO 2016

Catalyst-controlled wacker-type oxidation: Facile access to functionalized aldehydes

The aldehyde-selective oxidation of alkenes bearing diverse oxygen groups in the allylic and homoallylic position was accomplished with a nitrite-modified Wacker oxidation. Readily available oxygenated alkenes were oxidized in up to 88% aldehyde yield and as high as 97% aldehyde selectivity. The aldehyde-selective oxidation enabled the rapid, enantioselective synthesis of an important pharmaceutical agent, atomoxetine. Finally, the influence of proximal functional groups on this anti-Markovnikov reaction was explored, providing important preliminary mechanistic insight.

ALDEHYDE-SELECTIVE WACKER-TYPE OXIDATION OF UNBIASED ALKENES

This disclosure is directed to methods of preparing organic aldehydes, each method comprising contacting a terminal olefin with an oxidizing mixture comprising: (a) a dichloro-palladium complex; (b) a copper complex; (c) a source of nitrite; under aerobic reaction conditions sufficient to convert at least a portion of the terminal olefin to an aldehyde.