C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
C07D 221/28 (2006.01) C07D 489/02 (2006.01)
Patent
CA 2745410
The present disclosure generally relates to a process for converting a fused, tricyclic compound to a fused, tetracyclic compound that includes a furan ring therein. More particularly, the present disclosure related to a process for preparing a hydrocodone compound, or a compound structurally related thereto, and in particular (+)-hydrocodone, by subjecting a structurally corresponding sinomenine starting compound to a super acid-assisted furan ring closure reaction. Formula I, II. Examples of super acids useful in the processes described herein include, but are not limited to, trifluoromethanesulfonic acid (CF3SO3H), tetrafluoroboric acid (HBF4), fluorophosphoric acid (HPF6), fluorosulfuric acid (FSO3H). and fluoroantimonic acid (HSbF8), fluorophosphoric acid (FP(O)(OH)2) as well as combinations thereof.
La présente invention concerne d'une manière générale un procédé de conversion d'un composé tricyclique condensé en un composé tétracyclique condensé qui contient un cycle furane. L'invention concerne plus particulièrement un procédé de préparation d'un composé hydrocodone, ou d'un composé structurellement apparenté à l'hydrocodone, et en particulier le composé (+)-hydrocodone, le procédé consistant à soumettre un composé de départ sinoménine structurellement correspondant à une réaction de fermeture de cycle furane facilitée par un superacide. Formule I, II. Des exemples de superacides utiles dans les procédés de la présente invention comprennent, sans caractère limitatif, l'acide trifluorométhanesulfonique (CF3SO3H), l'acide tétrafluoroborique (HBF4), l'acide hexafluorophosphorique (HPF6), l'acide fluorosulfurique (FSO3H), ainsi que l'acide fluoroantimonique (HSbF8), l'acide fluorophosphorique (FP(O)(OH)2), et leurs combinaisons.
Jiang Tao
Liao Subo
Moore Erin
Wang Peter X.
Mallinckrodt Inc.
Osler Hoskin & Harcourt Llp
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