반응 #70361

반응 방정식

androstane-3β,5α,17β-triol

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title compound

5α-Hydroxyandrostane-3,17-dione

용매

DMSO

반응 조건

후처리

1. 1
   기타quenched at room temperature by addition of H2O (40 mL)
2. 2
   여과the mixture was filtered
3. 3
   세척the cake was washed with EtOAc
4. 4
   기타The layers were separated
5. 5
   추출the aqueous phase was extracted with EtOAc (3×40 mL)
6. 6
   건조The combined organic extracts were dried over Na2SO4
7. 7
   기타evaporated to dryness
8. 8
   기타The residue was purified by flash chromatography (SiO2, n-hexane/CH2Cl2/acetone 60/20/20)

실험 절차

A solution of androstane-3β,5α,17β-triol (0.48 g) and IBX (0.72 g) in DMSO (8 mL) was stirred at −15° C. overnight and then quenched at room temperature by addition of H2O (40 mL). After stirring for 15 min, the mixture was filtered and the cake was washed with EtOAc. The layers were separated, and the aqueous phase was extracted with EtOAc (3×40 mL). The combined organic extracts were dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (SiO2, n-hexane/CH2Cl2/acetone 60/20/20) to give the title compound II-aa (0.36 g, 75%). 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 3.48 (1H, s), 2.72 (1H, d), 2.60-1.18 (20H, m), 1.23 (3H, s), 0.86 (3H, s).

출처