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

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.

1. additionwere mixed under a nitrogen atmosphere
2. customThe reaction was terminated by the addition of diluted hydrochloric acid (approximately 5 mL)
3. additionThis solution was added to water (100 mL)
4. extractionextracted with ethyl acetate (3 times with 50 mL)
5. washwashed several times with saturated sodium bicarbonate solution (50 ml), saturated sodium chloride solution (two times with 50 mL,) and water (50 mL)
6. dry with materialThe organic layer was dried over magnesium sulfate
7. customthe solvent removed by rotary evaporation

ORD record

ord-05f05b2b3b804855b7dd1815838227e4

Source dataset

uspto-grants-1995_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05461042