1426125-45-2Relevant articles and documents
Selection and scale-Up evaluation of an alternative route to (-)-(3R,4R)-1-Benzyl-4-(benzylamino)piperidin-3-ol
Young, Ian S.,Ortiz, Adrian,Sawyer, James R.,Conlon, David A.,Buono, Frederic G.,Leung, Simon W.,Burt, Justin L.,Sortore, Eric W.
, p. 1558 - 1565 (2012)
An efficient, scalable synthesis of (-)-(3R,4R)-1-benzyl-4-(benzylamino) piperidin-3-ol (4) is described. Reduction of the pyridinium salt prepared from pyridine and benzyl chloride generated the corresponding tetrahydropyridine derivative. A two-stage epoxidation, followed by ring-opening of the epoxide with BnNH2, established the regiochemistry of the amino alcohol and served to set the trans-relationship between the amine and the hydroxyl group. The resulting racemic intermediate was then resolved by salt formation with (R)-O-acetyl mandelic acid. The process produced the O-acetyl mandelic acid salt of (-)-4 in 27% overall yield from benzyl chloride.