Abstract Cold as well as [3 H]-labelled substrates and metabolites IX-XI, XV, XVI, XX-XXII, XXIV, XXV and XXVIII were prepared by catalytic hydrogenation of epitestosterone (VIII) and∆ 1-dehydroepitestosterone (XIII). The key step in the preparation of compound XXVIII was reaction of 3β-tosylates XXVI and XXX with potassium nitrite in dimethyl sulfoxide.
[Concepcion, J. I.; Francisco, C. G.; Freire, R.; Hernandez, R.; Salazar, J. A.; Suarez, E. Journal of Organic Chemistry, 1986 , vol. 51, # 3 p. 402 - 404]