342403-52-5

Upstream product

• 91-02-1 phenyl(pyridin-2-yl)methanone 
• 67-68-5 dimethyl sulfoxide 
• 5005-36-7 phenyl-pyridin-2-yl-acetonitrile 
• 627-30-5 1-chloro-3-hydroxypropane 
• 101-82-6 2-Benzylpyridine 

Relevant academic research and scientific papers

Transition-Metal Free Chemoselective Hydroxylation and Hydroxylation-Deuteration of Heterobenzylic Methylenes

We developed an approach for direct selective hydroxylation of heterobenzylic methylenes to secondary alcohols avoiding overoxidation to ketones by using a KOBu-t/DMSO/air system. Most reactions could reach completion in several minutes to give hydroxylated products in 41-76% yields. Using DMSO-d6, this protocol resulted in difunctionalization of heterobenzylic methylenes to afford α-deuterated secondary alcohols (>93% incorporation). By employing this method, active pharmaceutical ingredients carbinoxamine and doxylamine were synthesized in two steps in moderate yields.

Reaction of 4-(N,N-dimethylamino)-2-phenyl-2-(2-pyridyl)butanenitrile and related compounds with ethyl chloroformate; formation of indolizinium and quinolizinium chlorides

4-(N,N-Dialkylamino)-2-phenyl-2-(2-pyridyl)butanenitriles (10, 11 and 12) and 5-(N,N-dimethylamino)-2-phenyl-2-(2-pyridyl)pentanenitrile (13) react with ethyl chloroformate, via a cyclization-N-dealkylation process, to give indolizinium and quinolizinium salts (1 and 2). Compounds 1 and 2 are also obtained by reaction of the alcohol derivatives 14 and 15 with thionyl chloride. Reaction of 2-phenyl-2-(2-pyridyl)ethanenitrile (9) in the presence of potassium hydroxide in dimethyl sulfoxide, leading to [2-hydroxy-2-phenyl-2-(2-pyridyl)ethyl]methylsulfoxide (21), is also described.