Cu-catalyzed N-arylation of oxazolidinones: an efficient synthesis of the kappa-opioid receptor Agonist CJ-15161.
An efficient method for intermolecular N-arylation of oxazolidinones using catalytic copper in the presence of a bidentate ligand is reported. The conditions allow the use of copper and can be used to prepare enantiopure N-aryl beta-amino alcohols. A short, scalable synthesis of CJ-15,161 is also reported. The required amines were obtained from the precursor alpha-amino acids or, more conveniently, from the corresponding 1,2-amino alcohols.
Ghosh
Arun
A
Chemical Research and Development, Pfizer Global Research and Development, Eastern Point Road, P.O. Box 8013, Groton, CT 06340-8013, USA. arun.ghosh@pfizer.com
Sieser
Janice E
JE
Caron
Stéphane
S
Couturier
Michel
M
Dupont-Gaudet
Kristina
K
Girardin
Melina
M
D000586:Amination; D001965:Bromides / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D023303:Oxazolidinones / Q000138:chemical synthesis / Q000737:chemistry*; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D017473:Receptors, Opioid, kappa / Q000819:agonists*
D001965:Bromides; D023303:Oxazolidinones; D011759:Pyrrolidines; D017473:Receptors, Opioid, kappa; C464962:CJ-15161; D003300:Copper