Water → Atamestane

HRID 1415856Notes

Reaction equation

HRID 1415856 reaction equation
I[C@H: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>CN(C)C=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

Participants

5

Reactant 3

HCID 962WaterHCID 11125Lithium CarbonateHCID 111443782beta-Iodo-1alpha-methylandrost-4-ene-3,17-dione

Product 1

HCID 57050Atamestane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.13 g (5 mmol) of 2β-iodo-1α-methylandrost-4-ene-3,17-dione from a) is introduced to a suspension, preheated to 130° C., of 0.73 g (10 mmol) of lithium carbonate in 10 ml of dimethylformamide and stirred at this temperature for 1.5 hours. After cooling, the reaction solution is added to 30 ml of water, extracted with ethyl acetate and after drying on sodium sulfate is concentrated by evaporation. The crude product is chromatographed on silica gel with ethyl acetate/hexane as mobile solvent. After recrystallization from ethyl acetate, 1.1 g of 1-methylandrosta-1,4-diene-3,17-dione (74% of theory) of a melting point of 169° C. is obtained.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. customafter drying on sodium sulfate
  4. concentrationis concentrated by evaporation
  5. customThe crude product is chromatographed on silica gel with ethyl acetate/hexane as mobile solvent
  6. customAfter recrystallization from ethyl acetate, 1.1 g of 1-methylandrosta-1,4-diene-3,17-dione (74% of theory) of a melting point of 169° C.
  7. customis obtained

Sources & evidence

ORD record
ord-b8f210a7cc8143f7a6fd78c2ae75cbd8
Source dataset
uspto-grants-1999_06
Patent number
US05908944

Reaction notes

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