Androstane-3beta,5alpha,17beta-triol → HCID 14135097, 화합물

HRID 1912665노트

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HRID 1912665 반응식
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH2:9][C@:10]4([OH:21])[C@:15]3([CH3:16])[CH2:14][CH2:13][C@H:12]([OH:20])[CH2:11]4)[C@@H:6]1[CH2:5][CH2:4][C@@H:3]2[OH:22]>CS(C)=O>[OH:21][C@:10]12[CH2:11][C:12](=[O:20])[CH2:13][CH2:14][C@:15]1([CH3:16])[C@@H:17]1[C@H:7]([C@H:6]3[C@@:2]([CH2:19][CH2:18]1)([CH3:1])[C:3](=[O:22])[CH2:4][CH2:5]3)[CH2:8][CH2:9]2

참가 물질

3

반응물 1

HCID 14135090Androstane-3beta,5alpha,17beta-triol

생성물 1

HCID 14135097HCID 14135097, 화합물

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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-ad (0.36 g, 75%). 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 3.48 (s, 1H), 2.72 (d, 1H), 2.60-1.18 (m, 20H), 1.23 (s, 3H), 0.86 (s, 3H).

후처리

  1. customquenched at room temperature by addition of H2O (40 mL)
  2. filtrationthe mixture was filtered
  3. washthe cake was washed with EtOAc
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted with EtOAc (3×40 mL)
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. customevaporated to dryness
  8. customThe residue was purified by flash chromatography (SiO2, n-hexane/CH2Cl2/acetone 60/20/20)

출처 및 근거

ORD 기록
ord-78929096adcc44b7b9f097eebb3ec4f5
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609644B2

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