Реакция #70368

Уравнение реакции

6α-carboxyandrostane-3,17-dione

NH3

→

title compound

6α-Carbamoylandrostane-3,17-dione

Растворители

toluene

SOCl2

THF

Условия реакции

Обработка

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

Методика

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).

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