Dihydrotestosterone → HCID 68730165、化合物

HRID 1182885

反応式

HRID 1182885 の反応式
[CH3:1][C@@:2]12[C@H:12]3[CH2:13][CH2:14][C@:15]4([CH3:21])[C@@H:19]([OH:20])[CH2:18][CH2:17][C@H:16]4[C@@H:11]3[CH2:10][CH2:9][C@H:8]1[CH2:7][C:5](=[O:6])[CH2:4][CH2:3]2.[F:22][B-](F)(F)F.F[B-](F)(F)F.ClC[N+]12CC[N+](F)(CC1)CC2>CC(O)C>[F:22][C@@H:7]1[C:5](=[O:6])[CH2:4][CH2:3][C@@:2]2([CH3:1])[CH:8]1[CH2:9][CH2:10][C@@H:11]1[C@@H:12]2[CH2:13][CH2:14][C@@:15]2([CH3:21])[C@H:16]1[CH2:17][CH2:18][C@@H:19]2[OH:20]

参加物

4

反応物 2

HCID 10635DihydrotestosteroneHCID 2724933Selectfluor2 回

生成物 1

HCID 68730165HCID 68730165、化合物収率 4%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

A mixture of dihydrotestosterone (1.00 g), 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) or SELECTFLUOR® (1.92 g) in i-PrOH (35 ml) was refluxed for 18 h. After cooling, the resulting precipitate was filtered and the organic phase was washed with H2O and brine, dried over Na2SO4 and was evaporated to dryness. The crude reaction mixture was purified by flash chromatography (SiO2, n-hexane/acetone/EOAc 75/12.5/12.5) to give 4α-fluoro-17β-hydroxyandrostan-3-one (43 mg, 4% yield).

後処理

  1. temperaturewas refluxed for 18 h
  2. temperatureAfter cooling
  3. filtrationthe resulting precipitate was filtered
  4. washthe organic phase was washed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. customwas evaporated to dryness
  7. customThe crude reaction mixture
  8. customwas purified by flash chromatography (SiO2, n-hexane/acetone/EOAc 75/12.5/12.5)

出典と根拠

ORDレコード
ord-71a0f7b11f1d47418a16ad1e29568ed0
出典データセット
uspto-grants-2014_03
特許番号
US08664210B2

関連ノート

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