Reacción #70368

Ecuación de reacción

6α-carboxyandrostane-3,17-dione

NH3

→

title compound

6α-Carbamoylandrostane-3,17-dione

Disolventes

toluene

SOCl2

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   Temperaturawas cooled at 0° C.
3. 3
   workup.STIRRINGAfter stirring overnight at room temperature
4. 4
   Otrothe mixture was evaporated to dryness
5. 5
   workup.ADDITIONThe residue was treated with CH2Cl2 and H2O
6. 6
   Extracciónextracted with CH2Cl2
7. 7
   LavadoThe combined organic extracts were washed with 10% K2CO3 solution, brine
8. 8
   Secadodried over Na2SO4
9. 9
   Otroevaporated to dryness
10. 10
    OtroThe residue was purified by flash chromatography (SiO2, n-hexane/acetone 50/50)

Procedimiento

To a stirred suspension of 6α-carboxyandrostane-3,17-dione (1.20 g) in dry toluene (12 mL), SOCl2 (1.2 mL) was added. After stirring 5.5 h at 85° C. the solution was cooled at 0° C. and 2M NH3 solution in THF (6 mL) was added. After stirring overnight at room temperature, the mixture was evaporated to dryness. The residue was treated with CH2Cl2 and H2O and extracted with CH2Cl2. The combined organic extracts were washed with 10% K2CO3 solution, brine, dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (SiO2, n-hexane/acetone 50/50) to give the title compound II-af (720 mg, 60%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 7.27 (1H, bs), 6.78 (1H, bs), 2.50-0.72 (21H, m), 1.00 (3H, s), 0.80 (3H, s).

Fuente