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

HRID 1390755노트

반응식

HRID 1390755 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bfe354f776684146859fc33679b731f8
출처 데이터셋
uspto-grants-1979_02
특허 번호
US04139617

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