179386-43-7Relevant articles and documents
Experiences with commercial production scale operation of dissolving metal reduction using lithium metal and liquid ammonia
Joshi,Sutton,Carver,Blanchard
, p. 997 - 1002 (2005)
The final step which generates free base in the synthesis of Sumanirole Maleate (PNU-95666E) consists of a cryogenic dissolving metal reduction using lithium metal and liquid ammonia. This chemistry was new to the Pfizer API production plant. Due to the hazards associated with the handling of lithium metal and ammonia gas at cryogenic reaction temperature, special challenges were encountered related to the design of the equipment, choice and handling of materials, operations, waste treatment, and both safety and economic issues. The topics discussed in this article include the use of Li instead of Na or K, impact of the choice of physical form of lithium metal, design of the lithium addition apparatus, and problems experienced during the addition. We also discuss techniques for addition of ammonia to the reactor, evaporation of ammonia from the reaction mixture, options for ammonia disposal, and internal reuse of ammonia. Comments on hazards for this reaction are also provided. It is hoped that this document will be of benefit to other professionals who may want to develop and scale-up dissolving metal reduction processes.
Enantioselective synthesis of (R)-Sumanirole using organocatalytic asymmetric aziridination of an α,β-unsaturated aldehyde
Nemoto, Tetsuhiro,Hayashi, Minami,Xu, Dashuang,Hamajima, Akinari,Hamada, Yasumasa
, p. 1133 - 1137 (2014/09/17)
Herein we report an enantioselective synthesis of (R)-Sumanirole wherein an organocatalytic asymmetric aziridination of 2-nitrocinnamaldehyde was the key step.
Synthesis of the Selective D2 Receptor Agonist PNU-95666E from D-Phenylalanine Using a Sequential Oxidative Cyclization Strategy
Romero, Arthur G.,Darlington, William H.,McMillan, Moses W.
, p. 6582 - 6587 (2007/10/03)
Compound 1 (PNU-95666E) is a selective and high-affinity agonist at the dopamine D2 receptor subtype and is of interest as a potential agent for the treatment of Parkinson's disease. Requiring a synthetic route amenable to scale-up, a synthesis