title: An efficient synthesis of N3,4-diphenyl-5-(4-fluorophenyl)-2-isopropyl-1H-3-pyrrolecarboxamide, a key intermediate for atorvastatin synthesis.
abstract: An efficient synthesis of N3,4-diphenyl-5-(4-fluorophenyl)-2-isopropyl-1H-3-pyrrolecarboxamide, a key intermediate for the synthesis of an effective HMG-CoA reductase inhibitor atorvastatin, is described. The synthesis is based on the 1,3-dipolar cycloaddition reaction of mesoionic munchnone (1,3-oxazolium-5-olate) with N1,3-diphenyl-2-propynamide leading to N-benzyl pyrrole, and N-debenzylation using sodium in liquid ammonia as key steps.
authors.affiliation: Department of Chemistry, Indian Institute of Technology-Delhi, Hauz Khas, New Delhi 110-016, India. pramod@netearth.iitd.ac.in
authors.forename: Pramod S
authors.initials: PS
authors.lastname: Pandey
authors.forename: T
authors.initials: T
authors.lastname: Srinivasa Rao
mesh_terms: D000069059:Atorvastatin; D006538:Heptanoic Acids / Q000138:chemical synthesis*; D019161:Hydroxymethylglutaryl-CoA Reductase Inhibitors / Q000138:chemical synthesis; D011758:Pyrroles / Q000138:chemical synthesis*
chemical_list: D006538:Heptanoic Acids; D019161:Hydroxymethylglutaryl-CoA Reductase Inhibitors; D011758:Pyrroles; D000069059:Atorvastatin