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US 12,240,808 B2Granted
Process for the synthesis of calebin-a and its intermediates
OwnerMuhammed Majeed, Kalyanam Nagabhushanam +2inventors
InventorsMuhammed Majeed, Kalyanam Nagabhushanam, Nagarajan Muthukaman, Pentakota Paradesi Naidu
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Abstract
The invention discloses novel intermediates in the synthesis of Calebin A represented by formula 3. The invention also covers processes for the synthesis of Calebin-A and its analogs using compounds of formula 3.
Claims6
A compound of general formula 3 represented below
- wherein X is selected from the group consisting of Cl, Br, and I;
- and
- R is selected from the group consisting of OMe, and H.
A process for the preparation of Calebin-A, and its analogs represented by general formula 5, from general formula 3,
- comprising:
- a) reacting a compound of formula 1 with a compound of formula 2 in the presence of a solvent and sodium bicarbonate or in the presence of potassium iodide, potassium carbonate, and 1,2 dibromoethane to obtain a compound of formula 3
- b) reacting a compound of formula 3 with triphenyl phosphine (TPP), in the presence of a solvent under reflux, cooling, and then charging with sodium carbonate followed by a compound of formula 4 or reacting a compound of formula 3 with a compound of formula 4, in the presence of an organo catalyst and methanol to obtain a compound represented by formula 5:
- wherein, R is selected from the group consisting of OMe and H;
- and X is selected from the group consisting of Cl, Br, I, and H.
2 more elements
A process for the preparation of Calebin-A, and its analogs represented by general formula 5,
- wherein,
- R is selected from group consisting of OMe and H;
- comprising the steps of
- a) mixing hydroxy acetone represented by formula 6 with pyridine in a reaction flask containing dichloromethane and cooling to 0-5° C.;
- b) adding acetyl chloride to the reaction mixture slowly at a temperature of 0-5° C. and then stirring at room temperature for 5 hours;
- c) diluting the reaction mass with water and washing with brine;
- d) separating the organic layer to obtain a compound of formula 7,
- e) charging compound of formula 7 from step d) into a reaction flask containing a 1:1 (v/v) ethanol:water mixture, calcium hydroxide, and a compound of formula 4;
- f) heating the reaction mixture to 50° C. for 15 h and cooling the reaction mass after completion of reaction to produce a solid, followed by filtering the resultant solid;
- g) washing the resultant solid of step f) with an ethanol:water mixture, concentrating the reaction mixture and drying under vacuum to yield Calebin A or its analogs as represented by general formula 5.
7 more elements
Dependencies are inferred from the claim text.