Reacción #70359

Ecuación de reacción

mCPBA

3β-hydroxyandrost-4-en-17-one

Na2SO3

NaHCO3

→

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

Disolventes

CH2Cl2

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with CH2Cl2 (3×100 mL)
2. 2
   LavadoThe combined organic extracts were washed with H2O
3. 3
   Secadodried over Na2SO4
4. 4
   Otroevaporated to dryness
5. 5
   OtroThe residue was purified by flash chromatography (SiO2, n-hexane/CH2Cl2/acetone 60/20/20)

Procedimiento

To a stirred solution of 3β-hydroxyandrost-4-en-17-one (0.81 g) in CH2Cl2 (7.4 mL) cooled at 0° C., a solution of mCPBA (0.77 mg) in CH2Cl2 (13.6 mL) was added dropwise. After 0.5 h at 0° C. and 0.5 h at room temperature, a 10% aqueous solution of Na2SO3 was added. The mixture was neutralized by addition of 5% NaHCO3 solution and extracted with CH2Cl2 (3×100 mL). The combined organic extracts were washed with H2O, dried over Na2SO4, and evaporated to dryness. The residue was purified by flash chromatography (SiO2, n-hexane/CH2Cl2/acetone 60/20/20) to give 3β-hydroxy-5α,6α-epoxyandrostane-17-one (0.64 g, 75%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 4.62 (1H, d), 3.52 (1H, m), 2.87 (1H, d), 2.44-0.56 (19H, m), 1.00 (3H, s), 0.72 (3H, s).

Fuente