(1R)-2-[(3R,4S)-3-Methyl-4-(N-phenyl-N-propionylamino)piperidin-1-yl]-1-phenylethyl p-bromobenzoate and N-[(3R,4S)-1-[(2S)-2-(4-bromophenyl)-2-hydroxyethyl]-3-methyl-piperidin-4-yl]-N-phenylacrylamide

Acta Crystallogr C. 2002 Jun;58(Pt 6):o362-4. doi: 10.1107/s0108270102006443. Epub 2002 May 31.

Abstract

Both title compounds, C(30)H(33)BrN(2)O(3) and C(23)H(27)BrN(2)O(2), respectively, are brominated derivatives of the potent opioid cis-beta-hydroxy-3-methylfentanyl (ohmefentanyl). Ohmefentanyl has three asymmetric C atoms and, therefore, has eight possible stereoisomers. The absolute configurations of the title compounds were determined to assign the proper configuration of two of these stereoisomers and the compounds have the same stereochemistry at two of the three asymmetric C atoms.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Acrylamides / chemical synthesis
  • Acrylamides / chemistry*
  • Analgesics / chemical synthesis
  • Analgesics / chemistry*
  • Benzoates / chemical synthesis
  • Benzoates / chemistry*
  • Crystallography, X-Ray
  • Fentanyl / analogs & derivatives*
  • Fentanyl / chemical synthesis
  • Fentanyl / chemistry
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure
  • Piperidines / chemical synthesis
  • Piperidines / chemistry*
  • Stereoisomerism

Substances

  • (1)-2-((3,4)-3-Methyl-4-(N-phenyl-N-propionylamino)piperidin-1-yl)-1-phenylethyl p-bromobenzoate
  • Acrylamides
  • Analgesics
  • Benzoates
  • N-((3,4)-1-((2)-2-(4-bromophenyl)-2-hydroxyethyl)-3-methyl-piperidin-4-yl)-N-phenylacrylamide
  • Piperidines
  • Fentanyl