Chemical methods for the conversion of Prednisolone to 11-𝛽-hydroxy-1,4-androstadiene-3,17-dione

Journal of Chemical Sciences

Fatima Naaz²  Pinnama Reddy Surya Pratap³  Syed Shafi2¹  Nayakanti Devanna³ 

[1] Department of Chemistry, Faculty of Science, Jamia Hamdard, Hamdard Nagar, New Delhi 110 062, India$$;Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard, Hamdard Nagar, New Delhi 110 062, India$$;Department of Industrial Chemistry, Jawaharlal Nehru Technological University, Anantapur, India$$

关键词: Prednisolone;    11-𝛽-hydroxy-1;    4-androstadiene-3;    17-dione;    Chemical methods;    ZnCl2;    Stable Wittig ylide;    Reformatsky reaction;   

DOI  :  

来源: Indian Academy of Sciences

【 摘 要 】

Several microbial transformations of steroids to 17-keto cortisones through side chain cleavage have been presented in the literature; however, yields and product selectivity in these methods were low. In the present study, some new methods have been identified for the side chain cleavage of prednisolone (1) to form 11-𝛽-hydroxy-1,4-androstadiene-3,17-dione (11-𝛽-hydroxy ADD). Prednisolone upon reaction with zinc chloride in dry THF results in the formation of cleavage product in good yield (76%). 11-𝛽-hydroxy ADD (2) has been formed in moderate yield (60%) under the Reformatsky reaction conditions by reacting with zincate. While performing the Wittig reaction using stable ylides, again results in the formation of compound 2 in good yield (56%). Side chain cleavage of prednisolone was confirmed from the physical and analytical data and similar when compared with the literature reports.

【 授权许可】

Unknown