Journal of Chemical Sciences | |
Chemical methods for the conversion of Prednisolone to 11-ð›½-hydroxy-1,4-androstadiene-3,17-dione | |
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-ð›½-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-ð›½-hydroxy-1,4-androstadiene-3,17-dione (11-ð›½-hydroxy ADD). Prednisolone upon reaction with zinc chloride in dry THF results in the formation of cleavage product in good yield (76%). 11-ð›½-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
【 预 览 】
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