title: An efficient, optimized synthesis of fentanyl and related analogs.
abstract: The alternate and optimized syntheses of the parent opioid fentanyl and its analogs are described. The routes presented exhibit high-yielding transformations leading to these powerful analgesics after optimization studies were carried out for each synthetic step. The general three-step strategy produced a panel of four fentanyls in excellent yields (73-78%) along with their more commonly encountered hydrochloride and citric acid salts. The following strategy offers the opportunity for the gram-scale, efficient production of this interesting class of opioid alkaloids.
authors.affiliation: Physical and Life Sciences Directorate, Lawrence Livermore National Laboratory, Livermore, California, United States of America; Forensic Science Center, Lawrence Livermore National Laboratory, Livermore, California, United States of America.
authors.forename: Carlos A
authors.initials: CA
authors.lastname: Valdez
authors.affiliation: Physical and Life Sciences Directorate, Lawrence Livermore National Laboratory, Livermore, California, United States of America; Forensic Science Center, Lawrence Livermore National Laboratory, Livermore, California, United States of America.
authors.forename: Roald N
authors.initials: RN
authors.lastname: Leif
authors.affiliation: Physical and Life Sciences Directorate, Lawrence Livermore National Laboratory, Livermore, California, United States of America; Forensic Science Center, Lawrence Livermore National Laboratory, Livermore, California, United States of America.
authors.forename: Brian P
authors.initials: BP
authors.lastname: Mayer
mesh_terms: D000478:Alkylation; D000701:Analgesics, Opioid / Q000138:chemical synthesis*; D005283:Fentanyl / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D010084:Oxidation-Reduction
chemical_list: D000701:Analgesics, Opioid; D005283:Fentanyl