(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.
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.
Deschamps
Jeffrey R
JR
Laboratory for the Structure of Matter, Code 6030, Naval Research Laboratory, Washington, DC 20375, USA. deschamps@nrl.navy.mil
George
Clifford
C
Flippen-Anderson
Judith L
JL
D000178:Acrylamides / Q000138:chemical synthesis / Q000737:chemistry*; D000700:Analgesics / Q000138:chemical synthesis / Q000737:chemistry*; D001565:Benzoates / Q000138:chemical synthesis / Q000737:chemistry*; D018360:Crystallography, X-Ray; D005283:Fentanyl / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
C464681:(1)-2-((3,4)-3-Methyl-4-(N-phenyl-N-propionylamino)piperidin-1-yl)-1-phenylethyl p-bromobenzoate; D000178:Acrylamides; D000700:Analgesics; D001565:Benzoates; C464682:N-((3,4)-1-((2)-2-(4-bromophenyl)-2-hydroxyethyl)-3-methyl-piperidin-4-yl)-N-phenylacrylamide; D010880:Piperidines; D005283:Fentanyl