Dihydrotestosterone → HCID 68730165, 화합물

HRID 1182885

반응식

HRID 1182885 반응식
[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]

참가 물질

4

반응물 2

HCID 10635DihydrotestosteroneHCID 2724933Selectfluor2회

생성물 1

HCID 68730165HCID 68730165, 화합물수율 4%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-71a0f7b11f1d47418a16ad1e29568ed0
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08664210B2

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