Practical and high-yield syntheses of dihydromorphine from tetrahydrothebaine and efficient syntheses of (8S)-8-bromomorphide.
A practical method for the conversion of tetrahydrothebaine to dihydromorphine in 92% yield is described. The procedure should allow more efficient production of opium products and may be easily modified for large-scale synthesis. The conversion of codeine to (8S)-8-bromomorphide, a potentially valuable intermediate to 6-demethoxyoripavine and derivatives, is also described. The absolute configuration of (8S)-8-bromomorphide was determined by a single-crystal X-ray diffraction study of the hydrobromide salt.
Przybyl
Anna K
AK
Laboratory of Medicinal Chemistry, Building 8, Room B1-22, National Institutes of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, 8 Center Drive, MSC 0815, Bethesda, Maryland 20892, USA.
Flippen-Anderson
Judith L
JL
Jacobson
Arthur E
AE
Rice
Kenner C
KC
D002384:Catalysis; D002855:Chromatography, Thin Layer; D018360:Crystallography, X-Ray; D004090:Dihydromorphine / Q000032:analysis / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D015394:Molecular Structure; D009022:Morphine Derivatives / Q000032:analysis / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013797:Thebaine / Q000031:analogs & derivatives / Q000737:chemistry
C476097:8-bromomorphide; D007202:Indicators and Reagents; D009022:Morphine Derivatives; D013797:Thebaine; D004090:Dihydromorphine