1419073-45-2

Upstream product

• 109-72-8 n-butyllithium 
• 13057-19-7 Iodomethyl methyl ether 
• 143919-46-4 1,2,3,4-tetrahydro-1,3-dimethyl-4-<3-(1-methylethoxy)phenyl>pyridine 

Relevant academic research and scientific papers

Diastereoselective syntheses of (3 R*,4 R*)- and (3 R*,4 S*)-4-Aryl-3-methyl-4-piperidinemethanol and fluoro analogues

Two concise and high-yielding diastereoselective syntheses of 4-aryl-3-methyl-4-piperidinemethanols were realized from 1,3-dimethyl-4- piperidinone. The key reactions to control the C3-C4 relative stereochemistry were the alkoxymethylation of a metalloenamine generated from 4-aryl-3-methyl-1,2,3,6-tetrahydropyridine that afforded the (3R*,4S*)-form and the nucleophilic substitution of a fluoroarene with deprotonated 3-methyl-4-piperidinenitrile giving the (3R*,4R*)- isomer. The corresponding fluoromethyl analogues were subsequently obtained through the fluorination of the piperidinemethanols using DAST.