2,4,6-Trimethylpyridine → HCID 15097998, compound

Participants

Reaction Conditions

Reaction Steps

70 g (0.147 mol) of the above-obtained 3β-tosyloxy-5α,6β-dihydroxy-17-oxo-androstane are dissolved in 350 ml. of collidine and the reaction mixture is heated in a nitrogen atmosphere, under stirring for 1.5 hours in an oil bath of 160° C. The collidine is then distilled off under reduced pressure, the evaporation residue is triturated with 400 ml. of water, filtred and washed with 10% aqueous hydrochloric acid solution, then with water to remove the last traces of collidine. The so-obtained product is dried in vacuo over phosphorous pentoxide at 40° C, and may be purified, if desired, by mixing with a fivefold amount of diethyl ether. 45 g of 5α,6β-dihydroxy-17-oxo-androst-2-ene (90%) are obtained; m.p. 183°-186° C; [α]D25 = +81° (c = 1 in chloroform).

Provenance & Evidence