Details

Autor(en) / Beteiligte

• Hosztafi, Sándor
• Marton, János

Titel

Synthesis of 1-fluoro-substituted codeine derivatives

Ist Teil von

• Chemical papers, 2016-07, Vol.70 (7), p.973-982

Ort / Verlag

Cham: Springer International Publishing

Erscheinungsjahr

2016

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Syntheses of new N -demethyl- N -substituted analogues (propyl, allyl) of 1-fluorocodeine and their 7,8-dihydro derivatives were described starting from codeine. 1-Fluoronorcodeine and 1-fluorodihydronorcodeine were prepared by N -demethylation with α-chloroethyl chloroformate from the corresponding 6- O -acetyl protected derivatives. 3- O -Demethylation of 1-fluorocodeine and 1-fluorodihydrocodeine with boron tribromide resulted in 1-fluoromorphine and 1-fluorodihydromorphine respectively. 1-Fluorodihydromorphine was acetylated to 3,6-di- O -acetyl-1-fluorodihydromorphine. 8-Fluoroapocodeine and N -propyl-8-fluoroapocodeine were synthesized from the appropriate 1-fluorocodeine derivatives by acid-catalyzed rearrangement.