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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.