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Patent / Jan 01, 2018

Preparation of umeclidinium bromide

  • Nuno Torres
  • Luis Sobral
  • Rafael Antunes
  • Maria Santos
  • Margarida Espadinha
WO 2018087561 A1 20180517

The present invention discloses processes for prepg. the title compd. I starting from the reaction of Et isonipecotate with 1-bromo-2-chloroethane in the presence of an org. base in a solvent to form Et 1-(2-chloroethyl)piperidine-4-carboxylate (II) or a salt thereof. II is then reacted with LDA in a solvent to form Et 1-azabicyclo[2.2.2]octane-4-carboxylate (III). III interacts with PhLi to form 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (IV), which is added to [(2-bromoethoxy)methyl]benzene to give I. Pharmaceutical compns. of I are also disclosed for treating respiratory diseases such as COPD and asthma.