Benzene → 17beta,19-Dihydroxy-1alpha,7alpha-dimethyl-5-androsten-3-one diacetate

HRID 1390755ノート

反応式

HRID 1390755 の反応式
[C:1]([OH:4])(=[O:3])[CH3:2].[C:5]([OH:8])(=[O:7])[CH3:6].[OH:9][C@H:10]1[CH2:15][CH2:14][C@H:13]2[C@H:16]3[C@H:27]([CH2:28][CH2:29][C@:11]12[CH3:12])[C@:24]1([CH2:25][OH:26])[C:19](=[CH:20][C:21](=[O:31])[CH2:22][C@@H:23]1[CH3:30])[CH:18]=[CH:17]3.[CH3:32][Cu]C.[Li].[Cl-].[NH4+].C1C=CC=CC=1>O1CCCC1>[C:1]([OH:4])(=[O:3])[CH3:2].[C:5]([OH:8])(=[O:7])[CH3:6].[OH:9][C@H:10]1[CH2:15][CH2:14][C@H:13]2[C@H:16]3[C@H:27]([CH2:28][CH2:29][C@:11]12[CH3:12])[C@:24]1([CH2:25][OH:26])[C:19]([CH2:20][C:21](=[O:31])[CH2:22][C@@H:23]1[CH3:30])=[CH:18][C@H:17]3[CH3:32]

参加物

6

反応物 4

HCID 241BenzeneHCID 25517Ammonium ChlorideHCID 8673474317beta, 19-Dihydroxy-1alpha-methyl-4,6-androstadien-3-one diacetateHCID 178477771HCID 178477771、化合物

生成物 1

HCID 8673631317beta,19-Dihydroxy-1alpha,7alpha-dimethyl-5-androsten-3-one diacetate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 17β, 19-dihydroxy-1α-methyl-4,6-androstadien-3-one diacetate in anhydrous tetrahydrofuran is slowly added to an ice cold ethereal solution of lithium dimethylcopper prepared as in the preceding Example. Stirring is continued for an additional 30 minutes and the mixture is poured onto a saturated aqueous ammonium chloride solution. Benzene is added and the mixture filtered through a bed of diatomaceous earth. The organic layer is separated, washed with aqueous ammonium chloride, washed with water, dried over magnesium sulfate and evaporated to dryness. The residue is chromatographed on a silica gel column and eluted with benzene. The eluant is evaporated and the residue recrystallized from a hexane solution to yield 17β,19-dihydroxy-1α,7α-dimethyl-5-androsten-3-one diacetate.

後処理

  1. filtrationthe mixture filtered through a bed of diatomaceous earth
  2. customThe organic layer is separated
  3. washwashed with aqueous ammonium chloride
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness
  7. customThe residue is chromatographed on a silica gel column
  8. washeluted with benzene
  9. customThe eluant is evaporated
  10. customthe residue recrystallized from a hexane solution

出典と根拠

ORDレコード
ord-bfe354f776684146859fc33679b731f8
出典データセット
uspto-grants-1979_02
特許番号
US04139617

反応ノート

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