Benzene → 17beta, 19-Dihydroxy-1alpha,7alpha-dimethyl-4-androsten-3-one diacetate

HRID 371856노트

반응식

HRID 371856 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](=[CH:20][C:21](=[O:31])[CH2:22][C@@H:23]1[CH3:30])[CH2:18][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 8673474217beta, 19-Dihydroxy-1alpha,7alpha-dimethyl-4-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 added slowly to an ice cold ethereal solution of lithium dimethylcopper prepared as in the preceding Example. Stirring is continued for 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 washed with aqueous ammonium chloride, water, dried over magnesium sulfate and evaporated to dryness. The residue is stirred at room temperature with aqueous methanolic hydrochloric acid for 1 hour and then poured onto ice water. The gum is extracted with ether, washed with water, dried over magnesium sulfate and the ether removed. The residue is chromatographed on silica gel and eluted with benzene. The eluant is recrystallized from hexane to give 17β,19-dihydroxy-1α,7α-dimethyl-4-androsten-3-one diacetate.

후처리

  1. filtrationthe mixture filtered through a bed of diatomaceous earth
  2. washThe organic layer is washed with aqueous ammonium chloride, water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness
  5. stirringThe residue is stirred at room temperature with aqueous methanolic hydrochloric acid for 1 hour
  6. additionpoured onto ice water
  7. extractionThe gum is extracted with ether
  8. washwashed with water
  9. dry with materialdried over magnesium sulfate
  10. customthe ether removed
  11. customThe residue is chromatographed on silica gel
  12. washeluted with benzene
  13. customThe eluant is recrystallized from hexane

출처 및 근거

ORD 기록
ord-b45c5b6585e2400a9505956a4c02219b
출처 데이터셋
uspto-grants-1978_05
특허 번호
US04087524

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