Process for the preparation of (-) -delta...

Details Process for the preparation of (-) -delta... Process for the preparation of (-) -delta...

C - Chemistry, Metallurgy

07

D

C07D 311/80 (2006.01)

Patent

CA 2751741

The present disclosure is directed to a process for the chemical syn-thesis of (-)-.DELTA.9- ^tetrahydrocannabinol (.DELTA.9--THC) and related compounds of formula (I). In particular, the process comprises a one-pot condensation and sulfonylatton re-action sequence that produces crude .DELTA.9--THC aryl sulfonate or related compounds. Sulfo.pi.ylatio.pi. of .DELTA.9-THC or related com-pounds immediately upon their formation imparts stability to the cannabinoids, and prevents formation of the corresponding .DELTA.8 isomer. .DELTA.9THC aryl sulfonates may be readily separated from A6THC aryl sul-fonates using reverse phase chromatogra-phy. Hydrolysis of the .DELTA.9-THC aryl sul-fonates or related compounds produces .DELTA.9--THC or related compounds containing rel-atively low amounts of the corresponding .DELTA.8 isomer. (Formula I).

La présente invention concerne un procédé de synthèse chimique du (-)-?9- tétrahydrocannabinol (?9-THC) et autres composés apparentés de formule (I). En particulier, le procédé comprend une séquence de réaction monotope de condensation et de sulfonylation qui produit un arylsulfonate de ?9-THC brut ou autres composés apparentés. Immédiatement lors de leur formation, la sulfonylation du ?9-THC ou autres composés apparentés confère la stabilité aux cannabinoïdes, et empêche la formation de l'isomère ?8 correspondant. Les arylsulfonates de ?9THC peuvent être facilement séparés des arylsulfonates de ?6THC par chromatographie en phases inversées. L'hydrolyse des arylsulphonates de ?9-THC ou autres composés apparentés donne un ?9-THC ou autres composés apparentés contenant des quantités relativement basses de l'isomère ?8 correspondant. (Formule I).

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