762273-01-8

Upstream product

• 3132-99-8 m-bromobenzoic aldehyde 
• 58824-55-8 1-(3-bromo-phenyl)-prop-2-en-1-ol 
• 676-58-4 methylmagnesium chloride 
• 75-16-1 methylmagnesium bromide 
• 762272-99-1 (+/-)-1-(3-bromophenyl)-3-(2-(2-hydroxypropan-2-yl)phenyl)-1-propanol 
• 762272-97-9 1-(3-bromophenyl)-3-[2-(1-hydroxy-1-methylethyl)phenyl]propan-1-one 
• 762272-95-7 2-[3-(3-bromophenyl)-3-hydroxypropyl]benzoic acid methyl ester 
• 165896-48-0 2-[3-(3-bromo-phenyl)-3-oxo-propyl]-benzoic acid methyl ester 

Downstream Products

• 1433669-59-0 2-(1-((((R)-1-(3-bromophenyl)-3-(2-(2-hydroxypropan-2-yl)phenyl)propyl)sulfanyl) methyl)cyclopropyl)acetonitrile 
• 866923-62-8 2-(1-((((R)-1-(3-((E)-2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-(2-(2-hydroxypropan-2-yl)phenyl)propyl)sulfanyl)methyl)cyclopropyl)acetonitrile 
• 158966-92-8 montelukast 
• 151767-02-1 Montelukast sodium 
• 1015076-76-2 C₁₉H₂₃BrO₄S 

Relevant academic research and scientific papers

New and practical synthesis of montelukast sodium, an antiasthmatic drug

A new and practical synthesis of montelukast sodium, an antiasthmatic drug, is described. The key steps are the synthesis of nitrile derivative 4 by chiral reduction of keto ester 9 using (-)-DIP-Cl, synthesis of vinylquinoline framework 16 by Wittig reaction, and Heck coupling of nitrile 4 with vinylquinoline 16. The method is operationally simple and suitable for the industrial production of the drug substance. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.

The palladium-catalyzed aerobic kinetic resolution of secondary alcohols: Reaction development, scope, and applications

The first palladium-catalyzed enantioselective oxidation of secondary alcohols has been developed, utilizing the readily available diamine (-)-sparteine as a chiral ligand and molecular oxygen as the stoichiometric oxidant. Mechanistic insights regarding the role of the base and hydrogen-bond donors have resulted in several improvements to the original system. Namely, addition of cesium carbonate and tert-butyl alcohol greatly enhances reaction rates, promoting rapid resolutions. The use of chloroform as solvent allows the use of ambient air as the terminal oxidant at 23°C, resulting in enhanced catalyst selectivity. These improved reaction conditions have permitted the successful kinetic resolution of benzylic, allylic, and cyclopropyl secondary alcohols to high enantiomeric excess with good-toexcellent selectivity factors. This catalyst system has also been applied to the desymmetrization of meso-diols, providing high yields of enantioenriched hydroxyketones.

A NEW PROCESS FOR THE PREPARATION OF MONTELUKAST

The present invention describes a novel process for the preparation of montelukast acid, and its pharmaceutically acceptable salts and esters.

The resolution of important pharmaceutical building blocks by palladium-catalyzed aerobic oxidation of secondary alcohols

The palladium-catalyzed aerobic oxidative kinetic resolution of key pharmaceutical building blocks is described. Substrates investigated are relevant to the enantioselective preparation of Prozac, Singulair, and the promising hNK-1 receptor antagonist from Merck. The latter provides the most selective aerobic oxidative kinetic resolution yet described.