Lithium Carbonate → Atamestane

HRID 275064

반응식

HRID 275064 반응식
C(=O)([O-])[O-].[Li+].[Li+].I[C@@H:8]1[C@H:25]([CH3:26])[C@@:24]2([CH3:27])[C:11]([CH2:12][CH2:13][C@@H:14]3[C@@H:23]2[CH2:22][CH2:21][C@@:19]2([CH3:20])[C@H:15]3[CH2:16][CH2:17][C:18]2=[O:28])=[CH:10][C:9]1=[O:29]>CN1CCCC1=O>[CH3:26][C:25]1[C@@:24]2([CH3:27])[C:11]([CH2:12][CH2:13][C@@H:14]3[C@@H:23]2[CH2:22][CH2:21][C@@:19]2([CH3:20])[C@H:15]3[CH2:16][CH2:17][C:18]2=[O:28])=[CH:10][C:9](=[O:29])[CH:8]=1

참가 물질

4

반응물 2

HCID 11125Lithium CarbonateHCID 677816322alpha-Iodo-1alpha-methylandrost-4-ene-3,17-dione

생성물 1

HCID 57050Atamestane수율 60%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

147.78 mg (2 mmol) of lithium carbonate is heated to 130° C. in 3 ml of N-methyl-pyrrolidone under nitrogen atmosphere. 426 mg (1 mmol) of 2α-iodo-1α-methyl-androst-4-ene-3,17-dione of example 3 is added to this preheated solution. The solution is stirred for another 2 hours at this temperature. After cooling to room temperature, the solution is added in 20 ml of ice water and the product is extracted with ethyl acetate. After evaporation of the solvent, the crude product is purified with ethyl acetate/hexane as mobile solvent by chromatography on silica gel. Concentration by evaporation of the fractions and recrystallization from ethyl acetate yields 178 mg (60% of theory) of 1-methylandrosta-1,4-diene-3,17-dione of melting point 169° C.

후처리

  1. extractionthe product is extracted with ethyl acetate
  2. customAfter evaporation of the solvent
  3. customthe crude product is purified with ethyl acetate/hexane as mobile solvent by chromatography on silica gel
  4. concentrationConcentration
  5. customby evaporation of the fractions and recrystallization from ethyl acetate

출처 및 근거

ORD 기록
ord-e048232aa518420dbe795277f166435a
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05391778

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