Water → Atamestane

HRID 275067

반응식

HRID 275067 반응식
I[CH:2]1[C@H:19]([CH3:20])[C@@:18]2([CH3:21])[C:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:17]2[CH2:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C:12]2=[O:22])=[CH:4][C:3]1=[O:23].C(=O)([O-])[O-].[Li+].[Li+].O>CN1CCCC1=O>[CH3:20][C:19]1[C@@:18]2([CH3:21])[C:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:17]2[CH2:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C:12]2=[O:22])=[CH:4][C:3](=[O:23])[CH:2]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 11125Lithium CarbonateHCID 677814542-Iodo-1alpha-methyl-androst-4-ene-3,17-dione2회

생성물 1

HCID 57050Atamestane

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

14.9 g of 2-iodo-1α-methyl-androst-4-ene-3,17-dione crude product of example 7 and 4.73 g (64 mmol) of anhydrous lithium carbonate are stirred in 95 ml of N-methyl-pyrrolidone for 1 hour at 130° C. under nitrogen atmosphere. After cooling of the reaction solution it is added to 0.6 1 of water and the product is extracted 3 times with 450 ml of ethyl acetate. The combined ethyl acetate phases are dried on sodium sulfate and then concentrated by evaporation. The residue is chromatographed on silica gel with ethyl acetate/hexane as mobile solvent. After concentration by evaporation of the fractions and recrystallization of the substance from ethyl acetate, 6.9 g of 1-methyl-androsta-1,4-diene-3,17-dione (69% of theory over 2 stages relative to 1α-methyl-androst-4-ene-3,17-dione in example 7) of melting point 168°-169° C. is obtained.

후처리

  1. temperatureAfter cooling of the reaction solution it
  2. extractionthe product is extracted 3 times with 450 ml of ethyl acetate
  3. dry with materialThe combined ethyl acetate phases are dried on sodium sulfate
  4. concentrationconcentrated by evaporation
  5. customThe residue is chromatographed on silica gel with ethyl acetate/hexane as mobile solvent
  6. concentrationAfter concentration
  7. customby evaporation of the fractions and recrystallization of the substance from ethyl acetate, 6.9 g of 1-methyl-androsta-1,4-diene-3,17-dione (69% of theory over 2 stages relative to 1α-methyl-androst-4-ene-3,17-dione in example 7) of melting point 168°-169° C.
  8. customis obtained

출처 및 근거

ORD 기록
ord-5fd1ac819c9b4f98ae03bab12d6e5197
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05391778

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