Continuous and convergent access to vicinyl amino alcohols.
Five active pharmaceutical ingredients (APIs) containing the vicinyl amino alcohol moiety were synthesized using a convergent chemical assembly system. The continuous system is composed of four flow reaction modules: biphasic oxidation, Corey-Chaykovsky epoxidation, phenol alkylation, and epoxide aminolysis. Judicious choice of reagents and module order allowed for two classes of β-amino alcohols, aryl and aryloxy, to be synthesized in good (27-69%) overall yields.
Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany. kerry.gilmore@mpikg.mpg.de peter.seeberger@mpikg.mpg.de.
Tomoya
T
Nobuta
Guozhi
G
Xiao
Diego
D
Ghislieri
Kerry
K
Gilmore
Peter H
PH
Seeberger
D000889:Anti-Arrhythmia Agents / Q000138:chemical synthesis; D000959:Antihypertensive Agents / Q000138:chemical synthesis; D001993:Bronchodilator Agents / Q000138:chemical synthesis; D060326:Chemistry Techniques, Synthetic; D004811:Epichlorohydrin / Q000737:chemistry; D004852:Epoxy Compounds / Q000138:chemical synthesis; D050198:Phenoxypropanolamines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000889:Anti-Arrhythmia Agents; D000959:Antihypertensive Agents; D001993:Bronchodilator Agents; D004852:Epoxy Compounds; D050198:Phenoxypropanolamines; D004811:Epichlorohydrin