Study On Synthesis Of Progesterone By Hypervalent Iodine Reagent

Hypervalent iodine reagent is a new type of oxidant, which has a special superiority in the pharmaceutical synthesis. The alcohols could been oxidized to the corresponding carbonyl compounds with high chemoselectivity by hypervalent iodine reagent. In our task the synthesis technology of hypervalent iodine reagent IBX( o-iodoxy-benzoic acid), DMP(Dess-Martin periodinane , the derivative of IBX) as well as the refine of DMP has been studied; and researches have also been done on the synthesis of progesterone using IBX, DMP and refined DMP as oxidants.The synthesis process of 2-iodobenzoic acid product and its derivative products were improved. Taking phthalic anhydride or its derivatives as raw materials, by three steps of hydrolysis, mercurilation and iodination, 2-iodobenzoic acid product or its derivative products were syntheticed. The route is feasible with easy operating, mild reaction conditions, economic and safe. As a economic and efficient cleaning reagent, the excellent characteristics of Oxone were showed in the synthesis of IBX and became the first choice in the synthesis of IBX. The reaction process and result were effected by the character of the substituent group in phenyl ring in the synthesis process of IBX derivatives. So the effect factor should be considered in choosing the raw materials. The synthesis of progesterone showed that the precursor of progesterone could been oxidized by hypervalent iodine reagent IBX, DMP and refined DMP, but the selectivity and yield is very different. The results were studied when the different solvents and different hypervalent iodine reagents were used and it was proved that the best process is as follows: refined DMP as the oxidant, dichloromethane as the solvent, the yield reached 87.0% and the content as 89.8%.It can be proved that comparing with the others, oxidation reaction by hypervalent iodine reagents has the following advantages, such as easily prepared, environmental friendly, mild reaction conditions, high chemoselectivity. It's feasible to synthetic the progesterone by using hypervalent iodine reagent IBX, DMP and refined DMP as oxidants.