Separation of tetrahydrocannabinols

Details Separation of tetrahydrocannabinols Separation of tetrahydrocannabinols

2008-01-22

2008-01-22

Dentz, Bernard (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

active

11132251

ABSTRACT:
An individual tetrahydrocannabinol isomer of interest is separated from a mixture containing two or more such isomers, by treating the mixture with an isocyanate or isothiocyanate of formula I:in-line-formulae description="In-line Formulae" end="lead"?R—(CH2)n—N═C═X  (I)in-line-formulae description="In-line Formulae" end="tail"?where R represents an aromatic ring optionally substituted with one or more electron withdrawing groups, n=0 or 1 and X is oxygen or sulphur; so as to produce a crystallizable THC carbamate of formula II:wherein X and R are as defined above, R′ is a C3-C10alkyl group and the dotted lines indicate optional unsaturation including aromatic, separating the compound of formula II from solution in isolation of other THC derivatives, and hydrolyzing the compound of formula II to form the individual tetrahydrocannabinol isomer of interest.

REFERENCES:
patent: 3636058 (1972-01-01), Fahrenholtz
Gaoni et al, JACS, 93(1), p. 217-224 (1971).
Powell G et al., “Science”, vol. 93 No. 2422 pp. 522-523 (1941).
Gaoni Y. and Mechoulan R., J.A.C.S. “Communications to the Editor”, vol. 86, pp. 1646-1647, (1964).

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