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

HRID 2397970ノート

反応式

HRID 2397970 の反応式
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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 887Methanol溶媒

実験手順

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 acetone-hexane yields 1α-methyl-4-androstene-17β,19-diol.

後処理

  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 acetone-hexane

出典と根拠

ORDレコード
ord-4d05452c6ca247f0b85211daee744714
出典データセット
uspto-grants-1977_05
特許番号
US04022769

反応ノート

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