Deuteration of Androstenedione by Use of Keto-Enol Tautomerization
Isotopic labeling of steroids has been done and marketed since the early 1980's. However, the United States has no current known manufacturer of labeled steroids. The deuteration of testosterone and androstenedione in particular were performed using two methods; deuteration utilizing keto-enol tautomerism in basic conditions, and by Moffatt Oxidation of labeled Testosterone at 40.0°C. Acidic conditions were also employed, but did not supply any deuteration. Results were characterized using Thin Layer Chromatography, IH and l3C Nuclear Magnetic Resonance, and Mass Spectroscopy data. Each method produced two to three deuterium atoms on the steroid. This method of production does not keep the deuterium from exchanging, however a process involving non-exchangeable deuterium is presented and explained.