反応 #70368

反応方程式

6α-carboxyandrostane-3,17-dione

NH3

→

title compound

6α-Carbamoylandrostane-3,17-dione

溶媒

toluene

SOCl2

THF

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   温度was cooled at 0° C.
3. 3
   workup.STIRRINGAfter stirring overnight at room temperature
4. 4
   その他the mixture was evaporated to dryness
5. 5
   workup.ADDITIONThe residue was treated with CH2Cl2 and H2O
6. 6
   抽出extracted with CH2Cl2
7. 7
   洗浄The combined organic extracts were washed with 10% K2CO3 solution, brine
8. 8
   乾燥dried over Na2SO4
9. 9
   その他evaporated to dryness
10. 10
    その他The residue was purified by flash chromatography (SiO2, n-hexane/acetone 50/50)

実験手順

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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