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- Title
Kinetics of Electrophilic Fluorination of Steroids and Epimerisation of Fluorosteroids.
- Authors
Rozatian, Neshat; Harsanyi, Antal; Murray, Ben J.; Hampton, Alexander S.; Chin, Emily J.; Cook, Alexander S.; Hodgson, David R. W.; Sandford, Graham
- Abstract
Fluorinated steroids, which are synthesised by electrophilic fluorination, form a significant proportion of marketed pharmaceuticals. To gain quantitative information on fluorination at the 6‐position of steroids, kinetics studies were conducted on enol ester derivatives of progesterone, testosterone, cholestenone and hydrocortisone with a series of electrophilic N−F reagents. The stereoselectivities of fluorination reactions of progesterone enol acetate and the kinetic effects of additives, including methanol and water, were investigated. The kinetics of epimerisation of 6β‐fluoroprogesterone to the more pharmacologically active 6α‐fluoroprogesterone isomer in HCl/acetic acid solutions are detailed.
- Subjects
FLUORINATION; ELECTROPHILES; STEROIDS; ANALYTICAL mechanics; ACID solutions; ENOLS; ESTER derivatives
- Publication
Chemistry - A European Journal, 2020, Vol 26, Issue 52, p12027
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202001120