Reacción #70380

Ecuación de reacción

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

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

i-PrOH

→

5α-hydroxyandrostane-3,6,17-trione

Rendimiento 75.0%

Disolventes

acetone

Jones reagent

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente