Collect. Czech. Chem. Commun. 1996, 61, 1037-1046
https://doi.org/10.1135/cccc19961037

One-Pot Deuteration and Reduction of Ketones in the Synthesis of [16,16,17-2H3]-Epitestosterone

Hana Chodounská, Alexander Kasal, David Šaman and Karel Ubik

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

Abstract

5α-Androstan-17-one and 6β-methoxy-3α,5-cyclo-5α-androstan-17-one were reduced by sodium in deuterium oxide to [16,16,17-2H3]-17β-alcohols. The 17β-tosyloxy group of [16,16,17-2H3]-6β-methoxy-3α,5-cyclo-5α-androstan-17β-ol tosylate was found to be stable under the conditions of the i-steroid rearrangement. The SN2 reaction of the 17β-tosyloxy group with potassium nitrite yielded the corresponding 17α-hydroxy derivative without any loss of deuterium.

Keywords: Steroid synthesis; Labelled epitestosterone.