Reaction #70380

Reaction equation

3β-hydroxy-5α,6α-epoxyandrostane-17-one

3β-hydroxy-5β,6β-epoxyandrostan-17-one

i-PrOH

→

5α-hydroxyandrostane-3,6,17-trione

Yield 75.0%

Solvents

acetone

Jones reagent

Conditions

Workup

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   Temperaturemaintaining the temperature below 40° C
3. 3
   workup.ADDITIONwas added and, after further 10 min
4. 4
   Filtrationthe suspension was filtered
5. 5
   Otherthe filtrate evaporated to dryness
6. 6
   workup.ADDITIONThe residue was treated with H2O (300 mL)
7. 7
   Extractionextracted with EtOAc (3×100 mL)
8. 8
   WashThe combined organic extracts were washed with H2O (100 mL), 5% aqueous NaHCO3 solution (100 mL), H2O (100 mL)
9. 9
   Dryingdried over Na2SO4
10. 10
    Otherevaporated to dryness

Procedure

To a solution of a 1/1 mixture of 3β-hydroxy-5α,6α-epoxyandrostane-17-one and 3β-hydroxy-5β,6β-epoxyandrostan-17-one (2.10 g, 6.90 mmol) in acetone (38 mL), Jones reagent (8.35 mL) was added dropwise, maintaining the temperature below 40° C. 5 min after completion of the addition, i-PrOH (10 mL) was added and, after further 10 min, the suspension was filtered and the filtrate evaporated to dryness. The residue was treated with H2O (300 mL) and extracted with EtOAc (3×100 mL). The combined organic extracts were washed with H2O (100 mL), 5% aqueous NaHCO3 solution (100 mL), H2O (100 mL), dried over Na2SO4 and evaporated to dryness to give 5α-hydroxyandrostane-3,6,17-trione as a white solid (1.65 g, 75%). 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 5.00 (1H, s), 2.85 (2H, m), 2.45-1.25 (17H, m), 1.06 (3H, s), 0.88 (3H, s).

Source