Studies on the Stereoselective Synthesis of cis-3-Methylfentanyl
Abstract
The potent synthetic opiate fentanyl can be prepared by reduction of an intermediate Schiff base or by decyanation of a suitable alpha aminonitrile. In the more potent 3-methyl-fentanyl series, the cis-isomer. Hence an attempt was made to develop an efficient stereoselective synthesis of the cis-isomer. Using sodium borohydride, Super-Hydride, Red-Al, and L-Selectride, the reduction of the appropriate Schiff base and the reductive decyanation of alpha- aminonitrile was studied. The ratio of the cis and trans-isomers formed in these reactions was determined by gas chromatograph. The cis-isomer predominated in all cases, with the selectivity being most pronounced for Selectride. Opioids, Fentanyls, Narcotic analgesics, Aromatic compounds, Reductive decyanation.
Document Details
- Document Type
- Technical Report
- Publication Date
- Jan 01, 1989
- Accession Number
- ADA205973
Entities
People
- C. P. Ferguson
- Fu-lian Hsu
- Harold D. Banks
- Peter W. Von Ostwalden
Organizations
- Youngstown State University