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

HRID 1834914노트

반응식

HRID 1834914 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 the above 17β,19-dihydroxy-1α-methyl-4-androsten-3-one 3-ethylenethioketal in methanol and the resulting suspension is refluxed for about 4 hours with rapid stirring. The suspension is cooled, filtered and the solvent evaporated. The residue is chromatographed on silica gel and eluted with methylenechloride. Recrystallization from acetonehexane yields 1α-methyl-4-androstene-17β,19-diol.

후처리

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

출처 및 근거

ORD 기록
ord-5d925dab140e4e5889863a774bfcf275
출처 데이터셋
uspto-grants-1978_01
특허 번호
US04071624

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