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Title: An Efficient, Optimized Synthesis of Fentanyl and Related Analogs

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. In conclusion, the following strategy offers the opportunity for the gram-scale, efficient production of this interesting class of opioid alkaloids.
Authors:
 [1] ;  [1] ;  [1] ;  [2]
  1. Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States)
  2. Bangor Univ. (United Kingdom)
Publication Date:
Report Number(s):
LLNL-JRNL-656516
Journal ID: ISSN 1932-6203
Grant/Contract Number:
AC52-07NA27344
Type:
Accepted Manuscript
Journal Name:
PLoS ONE
Additional Journal Information:
Journal Volume: 9; Journal Issue: 9; Journal ID: ISSN 1932-6203
Publisher:
Public Library of Science
Research Org:
Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States)
Sponsoring Org:
USDOE
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; oils; chlorides; column chromatography; methylenes; citric acid; ethers; opioids; anhydrides; fentanyl; acetylfentanyl; thiofentanyl; acetylthiofentanyl; sublimaze
OSTI Identifier:
1418961

Valdez, Carlos A., Leif, Roald N., Mayer, Brian P., and Lahmann, Martina. An Efficient, Optimized Synthesis of Fentanyl and Related Analogs. United States: N. p., Web. doi:10.1371/journal.pone.0108250.
Valdez, Carlos A., Leif, Roald N., Mayer, Brian P., & Lahmann, Martina. An Efficient, Optimized Synthesis of Fentanyl and Related Analogs. United States. doi:10.1371/journal.pone.0108250.
Valdez, Carlos A., Leif, Roald N., Mayer, Brian P., and Lahmann, Martina. 2014. "An Efficient, Optimized Synthesis of Fentanyl and Related Analogs". United States. doi:10.1371/journal.pone.0108250. https://www.osti.gov/servlets/purl/1418961.
@article{osti_1418961,
title = {An Efficient, Optimized Synthesis of Fentanyl and Related Analogs},
author = {Valdez, Carlos A. and Leif, Roald N. and Mayer, Brian P. and Lahmann, Martina},
abstractNote = {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. In conclusion, the following strategy offers the opportunity for the gram-scale, efficient production of this interesting class of opioid alkaloids.},
doi = {10.1371/journal.pone.0108250},
journal = {PLoS ONE},
number = 9,
volume = 9,
place = {United States},
year = {2014},
month = {9}
}