2,3,5-Triiodobenzoic acid → 5-Androstene-3 beta,7 beta,17 beta-triol

Participants

Reaction Steps

A solution of 3β,17β diacetoxyandrost-5-en-7-one (0.9581 g, 2.466 mmol) and pentane (30 mL), dried over MgSO4) were mixed under a nitrogen atmosphere. TIBA (9.5 mL, 9.5 mmol, 1M in toluene) was then added dropwise by syringe. The solution was stirred at room temperature for about 1 hour. The reaction was terminated by the addition of diluted hydrochloric acid (approximately 5 mL). This solution was added to water (100 mL) and extracted with ethyl acetate (3 times with 50 mL). The organic layers were combined and then washed several times with saturated sodium bicarbonate solution (50 ml), saturated sodium chloride solution (two times with 50 mL,) and water (50 mL). The organic layer was dried over magnesium sulfate and the solvent removed by rotary evaporation to yield 86% crude product. 1H NMR indicated that the crude product contained 3β,17β,-diacetoxy-7-β-hydroxyandrost-5-en-7-one (86%) and 3β,17β -diacetoxy-7-α-hydroxyandrost-5-ene.

Provenance & Evidence