Androstane-3beta,5alpha,17beta-triol → HCID 14135097、化合物

HRID 1912665ノート

反応式

HRID 1912665 の反応式
[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

参加物

3

反応物 1

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

生成物 1

HCID 14135097HCID 14135097、化合物

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

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-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).

後処理

  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)

出典と根拠

ORDレコード
ord-78929096adcc44b7b9f097eebb3ec4f5
出典データセット
uspto-grants-2013_12
特許番号
US08609644B2

反応ノート

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