反応 #70361

反応方程式

androstane-3β,5α,17β-triol

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title compound

5α-Hydroxyandrostane-3,17-dione

溶媒

DMSO

反応条件

後処理

1. 1
   その他quenched at room temperature by addition of H2O (40 mL)
2. 2
   ろ過the mixture was filtered
3. 3
   洗浄the cake was washed with EtOAc
4. 4
   その他The layers were separated
5. 5
   抽出the aqueous phase was extracted with EtOAc (3×40 mL)
6. 6
   乾燥The combined organic extracts were dried over Na2SO4
7. 7
   その他evaporated to dryness
8. 8
   その他The residue was purified by flash chromatography (SiO2, n-hexane/CH2Cl2/acetone 60/20/20)

実験手順

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).

出典