Water → 17beta-Acetoxy-l-methyl-androsta-1,4-dien-3-one

HRID 275071Notes

Reaction equation

HRID 275071 reaction equation
[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C:14](=[CH:15][C:16](=[O:26])[CH:17](I)[C@@H:18]1[CH3:24])[CH2:13][CH2:12]3)(=[O:3])[CH3:2].C(=O)([O-])[O-].[Li+].[Li+].O>CN(C)C=O>[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C:14](=[CH:15][C:16](=[O:26])[CH:17]=[C:18]1[CH3:24])[CH2:13][CH2:12]3)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 11125Lithium CarbonateHCID 6778185217beta-Acetoxy-2-iodo-1alpha-methyl-androst-4-en-3-one

Product 1

HCID 1042750517beta-Acetoxy-l-methyl-androsta-1,4-dien-3-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.4 g (3 mmol) of 17α-acetoxy-2-iodo-1α-methyl-androst-4-en-3-one of example 11 and 0.443 g (6 mmol) of anhydrous lithium carbonate are stirred in 6 ml of dimethylformamide for 1 hour at 120° C. under nitrogen atmosphere. After cooling, it is added to water and extracted with ethyl acetate. The ethyl acetate solution is 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, 0.95 g (92% of theory) of 17β-acetoxy-1-methyl-androsta-1,4-dien-3-one of melting point 173° C. is obtained.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. dry with materialThe ethyl acetate solution is 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, 0.95 g (92% of theory) of 17β-acetoxy-1-methyl-androsta-1,4-dien-3-one of melting point 173° C.
  8. customis obtained

Sources & evidence

ORD record
ord-f98ccbc914194730a661b3e8d4e4d3f8
Source dataset
uspto-grants-1995_02
Patent number
US05391778

Reaction notes

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