Collect. Czech. Chem. Commun. 1997, 62, 656-664

Dihydrotestosterone with an Ammonium Centre in the Position 16β

Barbora Slavíková, Alexander Kasal and Miloš Buděšínský

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic,166 10 Prague 6, Czech Republic


In an alternative synthesis of 17β-hydroxy-16β-(piperidin-1-yl)-5α-androstan-3-one (4), neighbouring group participation between a 17β-carbonyloxy group and the 16β-amino group was used and a high yield partial hydrolysis of 3β,17β-diacetoxy-16β-(piperidin-1-yl)-5α-androstane (11) was developed. Interference of the neighbouring group participation was also apparent in another 17β-acetoxy derivative - in oxidation of compound 12 to 13. Compound 4 was converted into water-soluble derivatives, i.e. quaternary ammonium derivatives 17 to 20.

Keywords: Neighbouring group participation; Hormone analogues; Quaternary ammonium salts.