Synthesis and analytics of 2,2,3,4,4-d5-19-nor-5α-androsterone—An internal standard in doping analysis

A short and efficient synthesis of pentadeuterated 2,2,3,4,4-d5-19-nor-5α-androsterone 7 starting from 19-norandrost-4-ene-3,17-dione 1 by a d1-l-Selectride mediated stereo- and regioselective reduction of the 3-keto group is presented. The use of compound 7 as internal standard for the detection of anabolic steroids via mass spectrometric techniques such as gas chromatography–mass spectrometry (GC–MS) is discussed.