반응 #70368

반응 방정식

6α-carboxyandrostane-3,17-dione

NH3

→

title compound

6α-Carbamoylandrostane-3,17-dione

용매

toluene

SOCl2

THF

반응 조건

후처리

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

실험 절차

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).

출처