Methanol → (RS)-Clopidogrel

Participants

Reaction Steps

1 g (0.00326 mol) (±)-(2-chlorophenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyrid-5-yl)acetamide was added to 2 mL toluene at 0° C. along with stirring, followed by dropwise addition of 1 mL titanium tetrachloride, and the reaction was stirred at 0° C. for 1 hour. Later 18 mL of methanol was added, and then the reaction was stirred for 36 hour at 29° C. and later reflux for 3 hrs. The solvent was distilled under reduced pressure and the residue was added to aq. sodium carbonate at 0° C. the product was extracted with 20 mL ethyl acetate, and the organic layer was isolated, dried over anhy. Na2SO4, concentrated and purified by column chromatography using hexane:ethyl acetate as eluent. The product obtained was stored under nitrogen atmosphere and kept in refrigerator before converting into salt. The yield of titled product was 0.157 g (12-15%).

Provenance & Evidence