Collect. Czech. Chem. Commun. 1996, 61, 1037-1046

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


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.