40116-79-8

Upstream product

• 3506-36-3 3-dimethylaminopropiophenone 
• 1270016-44-8 (R)-N,N-dimethylamino-1-phenylpropanol oxalate 
• 100306-33-0 (1R)-3-chloro-1-phenylpropanol 
• 5554-64-3 N,N-dimethyl-3-hydroxy-3-phenylpropylamine 
• 123-62-6 propionic acid anhydride 

Downstream Products

• 56225-81-1 N,N-dimethyl-3-phenyl-3-(4-(trifluoromethyl)phenoxy)-1-propylamine 
• 1270016-46-0 (R)-N,N-dimethyl-3-(2-methyl-(4-acetylphenyl)oxy)-3-phenyl-1-aminopropane 
• 162938-15-0 (R)-N-methyl-3-(2-methylthiophenoxy)-3-phenyl-propylamine 
• 114247-09-5 (R)-fluoxetine hydrochloride 
• 222961-69-5 [(R)-3-(2-Methanesulfinyl-phenoxy)-3-phenyl-propyl]-dimethyl-amine 

Relevant academic research and scientific papers

Amino alcohols using the optically active amino alcohol derivative bi- Nord complex boron - -

Disclosed are an amino alcohol-boron-binol complex as an intermediate, including Complex 3-1-1 shown below, and a method for preparing an optically active amino alcohol by using the same, wherein a racemic amino alcohol is resolved in an enationselective manner using a boron compound and a (R)- or (S)-binol, whereby an amino alcohol derivative with high optical purity can be prepared at high yield.

Towards practical earth abundant reduction catalysis: Design of improved catalysts for manganese catalysed hydrogenation

Manganese catalysts derived from tridentate P,N,N ligands can be activated easily using weak bases for both ketone and ester hydrogenations. Kinetic studies indicate the ketone hydrogenations are 0th order in acetophenone, positive order in hydrogen and 1st order in the catalyst. This implies that the rate determining step of the reaction was the activation of hydrogen. New ligand systems with varying donor strength were studied and it was possible to make the hydrogen activation significantly more efficient; a catalyst displaying around a 3-fold increase in initial turn-over frequencies for the hydrogenation of acetophenone relative to the parent system was discovered as a result of these kinetic investigations. Ester hydrogenations and ketone transfer hydrogenation (isopropanol as reductant) are first order for both the substrate and catalysts. Kinetic studies also gained insight into catalyst stability and identified a working range in which the catalyst is stable throughout the catalytic reaction (and a larger working range where high yields can still be achieved). The new more active catalyst, combining an electron-rich phosphine with an electron-rich pyridine is capable of hydrogenating acetophenone using as little as 0.01 mol% catalyst at 65 °C. In all, protocols for reduction of 21 ketones and 15 esters are described.

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

Synthesis of (R)-tembamide and (R)-aegeline via asymmetric transfer hydrogenation in water

The synthesis of (R)-tembamide and (R)-aegeline via asymmetric transfer hydrogenation involving enantioenriched monosulfonamide-RhCp a - complex in aqueous sodium formate as hydride donor is described.

NOVEL PROCESS FOR THE PREPARATION OF 4-HYDROXY ATOMOXETINE

The present invention relates to novel process for the preparation of 4-hydroxy Atomoxetine or its pharmaceutically acceptable salts thereof. The present invention also relates to novel intermediates used in the preparation of 4-hydroxy Atomoxetine.

Effects of methyl substituents on the activity and enantioselectivity of homobenzotetramisole-based catalysts in the kinetic resolution of alcohols

Substitution of the tetrahydropyrimidine ring in the enantioselective acyl transfer catalyst homobenzotetramisole (HBTM) 6 with methyl groups exerts a dramatic influence on its performance in the kinetic resolution of secondary alcohols. The syn-3-methyl analogue of HBTM (9a) has proved to be superior to the parent compound in terms of catalytic activity, enantioselectivity, and synthetic accessibility.

Enantioselective synthesis of lobeline via nonenzymatic desymmetrization

Lobeline has been prepared in enantiopure form via desymmetrization of lobelanidine with use of BTM, a nonenzymatic enantioselective acyl transfer catalyst.

Synthesis of ruthenium-hydride complexes and preparation procedures of chiral alcohols and ketones

trans-RuH(η1-BH4)[(S)-xylbinap][(S,S)-dpen] (0.00125 mmol), acetophenone (5.0 mmol), and 2-propanol (2.5 mL) were placed in an autoclave, and the resulting solution was repeatedly subject 5 times to a procedure of performing pressure reduction and argon introduction while stirring the solution for deaeration. A hydrogen tank was then connected to the autoclave, and after replacing the air inside an introduction tube with hydrogen, the pressure inside the autoclave was adjusted to 5 atmospheres and then hydrogen was released until the pressure dropped to 1 atmosphere. After repeating this procedure 10 times, the hydrogen pressure was adjusted to 8 atmospheres and stirring at 25° C. was performed for 12 hours. By concentrating the solution obtained by depressurization and subjecting the crude product to simple distillation, (R)-1-phenylethanol (yield: 95%) in the form of a colorless oily substance was obtained at an ee of 99%.

Process for preparing optically active secondary alcohols having nitrogenous or oxygenic functional groups

A process for preparing optically active secondary alcohols of the general formula (3), [wherein R1 is linear lower alkyl, an aromatic ring group, or the like; A is CH2NR2R3 or the like; n is an integer of 0 to 2; and * represents an asymmetric carbon atom] by asymmetrically hydrogenating a ketone compound of the general formula (1) having nitrogenous or oxygen functional group at any of the a-, β- and γ-positions, with selectivity among functional groups by the use of a ruthenium/optically active bidentate phosphine/diamine complex as the catalyst in the presence of hydrogen alone or together with a base. The optically active secondary alcohols obtained by the process are useful as drugs and intermediates for the preparation of drugs.

trans-RuH(η1-BH4)(binap)(1,2-diamine): A catalyst for asymmetric hydrogenation of simple ketones under base-free conditions

(Chemical Equqtion Presentation) Reaction of a chiral RuCl2(diphosphine)(1,2-diamine) complex and NaBH4 forms trans-RuH(η1-BH4)(diphosphine)(1,2-diamine) quantitatively. The TolBINAP/DPEN Ru complex has been characterized by single crystal X-ray analysis as well as NMR and IR spectra. The new Ru complexes allow for asymmetric hydrogenation of simple ketones in 2-propanol without an additional strong base. Various base-sensitive ketones are convertible to chiral alcohols in a high enantiomeric purity with a substrate/catalyst ratio of up to 100 000 under mild conditions. Configurationally unstable 2-isopropyl- and 2-methoxycyclohexanone can be kinetically resolved with a high enantiomer discrimination. This procedure overcomes the drawback of an earlier method using RuCl2(diphosphine)(diamine) and an alkaline base, which sometimes causes undesired reactions such as ester exchange, epoxy-ring opening, β-elimination, and polymerization of ketonic substrates. Copyright