Process and compounds for preparation of cannabinoids
AssigneeEmbio Limited
InventorsGollapudy SUBRAHMANYAM, Sunil JOSHI, Nilesh Liladhar BONDE, Jinesh Gajanand BHATT, Makarand Sitaram GORE
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Abstract
The invention involves condensation of various derivatives of cyclic alkene alcohols of Formula II or Formula III where, R1 is alkyl, aryl, alkyl aryl or heterocyclic carbamoyl. R2 is either R1 as mentioned earlier or an acyl group, —C(═O)—R3 where, R3 is selected from a group comprising (subst)C1-C12 alkyl, (subst)aryl, alkyl aryl with olivetol to get (−)-trans-Δ9-tetrahydrocannabinol (also known as Dronabinol, Formula I). The process disclosed provides high purity of dronabinol at crude stage making it easy for purification.
Claims28
A compound [C] having general formula as,
- which is a derivative of olefins wherein
- R1:
- alkyl, aryl, alkyl aryl, heterocyclic, alkyl heterocyclic sulfonyl carbamate or H,
- R2:
- alkyl, aryl, alkyl aryl, heterocyclic, alkyl heterocyclic sulfonyl carbamates or alkyl, aryl, Alkyl aryl, heterocyclic ester,
- R3:
- alkyl, aryl, alkyl aryl, heterocyclic, alkyl heterocyclic sulfonyl carbamates or alkyl, aryl, Alkyl aryl, heterocyclic esters.
A process for preparation of compound of Formula IV or VIII by condensation of menth-2-ene-1,8-diol or menth-1-ene-3,8-diol with alkyl/aryl/alkyl aryl/heteroaryl sulfonyl isocyanate, the reaction being carried out in organic solvents at temperature between −25° C. to +75° C.
A process for preparation of the compound of Formula XI by acylation of menth-1-ene-3,8-diol in organic solvents using carboxylic acids or its respective acid chloride, in the presence of coupling agents and organic or weak inorganic bases.
A process for preparing menth-1-ene-3,8-diol from menth-2-ene-1,8-diol. The method comprising steps of:
- treating the menth-2-ene-1,8-diol with oxidizing agent in organic aprotic solvents to obtain ketone between −50° C. to +50° C.;
- reducing the ketone obtained using hydride based reducing agent using Luche reduction condition in organic solvent.
Dependencies are inferred from the claim text.