17beta,19-Dihydroxy-1alpha-methyl-4-androsten-3-one 3-ethylenethioketal → 1alpha-Methyl-4-androstene-17beta,19-diol

HRID 1733089노트

반응식

HRID 1733089 반응식
C1O[C:4]2([CH2:21][C@H:20]([CH3:22])[C@@:19]3([CH2:23][OH:24])[C:6]([CH2:7][CH2:8][C@@H:9]4[C@@H:18]3[CH2:17][CH2:16][C@@:14]3([CH3:15])[C@H:10]4[CH2:11][CH2:12][C@@H:13]3[OH:25])=[CH:5]2)SC1>[Ni].CO>[CH3:22][C@@H:20]1[C@@:19]2([CH2:23][OH:24])[C:6]([CH2:7][CH2:8][C@@H:9]3[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[OH:25])=[CH:5][CH2:4][CH2:21]1

참가 물질

4

반응물 1

HCID 2279742417beta,19-Dihydroxy-1alpha-methyl-4-androsten-3-one 3-ethylenethioketal

생성물 1

HCID 705847581alpha-Methyl-4-androstene-17beta,19-diol

시약·촉매·용매 2

HCID 935Nickel촉매HCID 887Methanol용매

실험 절차

Raney nickel is added to a solution of 17β,19-dihydroxy-1α-methyl-4-androsten-3-one 3-ethylenethioketal in methanol and the resulting suspension is refluxed for four hours with rapid stirring. The suspension is cooled, filtered and the solvent evaporated. The remaining residue is chromatographed on silica gel and eluted with methylenechloride. Recrystallization from acetone-hexane yields the compound 1α-methyl-4-androstene-17β,19-diol.

후처리

  1. temperaturethe resulting suspension is refluxed for four hours with rapid stirring
  2. temperatureThe suspension is cooled
  3. filtrationfiltered
  4. customthe solvent evaporated
  5. customThe remaining residue is chromatographed on silica gel
  6. washeluted with methylenechloride
  7. customRecrystallization from acetone-hexane

출처 및 근거

ORD 기록
ord-cbfcb143d3224470bf11660ee88b0c4a
출처 데이터셋
uspto-grants-1980_12
특허 번호
US04239681

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