Water → Atamestane

HRID 275062

Reaction equation

HRID 275062 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 of example 1 is introduced in a suspension of 0.73 g (10 mmol) of lithium carbonate in 10 ml of dimethylformamide preheated to 130° C. and stirred for 1.5 hours at this temperature. After cooling, the reaction solution is added to 30 ml of water, extracted with ethyl acetate and after drying on sodium sulfate, 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 melting point 169° C. is obtained.

Workup

  1. custompreheated to 130° C.
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. customafter drying on sodium sulfate
  5. concentrationconcentrated by evaporation
  6. customThe crude product is chromatographed on silica gel with ethyl acetate/hexane as mobile solvent
  7. customAfter recrystallization from ethyl acetate, 1.1 g of 1-methylandrosta-1,4-diene-3,17-dione (74% of theory) of melting point 169° C.
  8. customis obtained

Sources & evidence

ORD record
ord-aa91c1a6b35442468f6d75d761b5b33b
Source dataset
uspto-grants-1995_02
Patent number
US05391778

Linked notes

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