Reacción #70401

Ecuación de reacción

7α-formylandrostane-3,17-dione

KMnO4

→

7α-carboxyandrostane-3,17-dione

Rendimiento 96.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   Otrothe mixture was quenched by addition of 40% aqueous NaHSO3 solution
3. 3
   FiltraciónThe suspension was filtered
4. 4
   Lavadowashed with H2O
5. 5
   Otrothe filtrate was freeze-dried
6. 6
   Extracciónextracted with EtOAc (4×70 mL)
7. 7
   SecadoThe combined organic extracts were dried over Na2SO4
8. 8
   Otroevaporated to dryness

Procedimiento

To a stirred suspension of 7α-formylandrostane-3,17-dione (1.77 g) in t-ButOH (35 mL) and 5% aqueous Na2HPO4 solution (21.5 mL), 1N aqueous KMnO4 (35 mL) was added. After 5 minutes at room temperature, the mixture was quenched by addition of 40% aqueous NaHSO3 solution. The suspension was filtered, washed with H2O and the filtrate was freeze-dried. The residue was taken up with H2O (50 mL) and extracted with EtOAc (4×70 mL). The combined organic extracts were dried over Na2SO4 and evaporated to dryness to give 7α-carboxyandrostane-3,17-dione (1.80 g, 96%). 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 12.00 (1H, bb), 2.65 (1H, m), 2.45-0.70 (20H, m), 1.00 (3H, s), 0.79 (3H, s).

Fuente