N-Iodosuccinimide → 2alpha-Iodo-1alpha-methylandrost-4-ene-3,17-dione

HRID 275063Notes

Reaction equation

HRID 275063 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]2[C@:20]([CH3:24])([C@@H:21]([CH3:23])[CH:22]=1)[C@@H:19]1[C@H:10]([C@H:11]3[C@@:15]([CH2:17][CH2:18]1)([CH3:16])[C:14](=[O:25])[CH2:13][CH2:12]3)[CH2:9][CH2:8]2)(=O)C.[I:26]N1C(=O)CCC1=O>CO>[I:26][C@@H:22]1[C@H:21]([CH3:23])[C@@:20]2([CH3:24])[C:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C:14]2=[O:25])=[CH:6][C:5]1=[O:4]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 108716113-Acetoxy-1alpha-methylandrosta-2,4-dien-17-one

Product 1

HCID 677816322alpha-Iodo-1alpha-methylandrost-4-ene-3,17-dioneYield 55.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.42 g (10 mmol) of 3-acetoxy-1α-methyl-androsta-2,4-dien-17-one (DE-A 3715869) is dissolved in 40 ml of absolute methanol. 2.25 g (10 mmol) of N-iodosuccinimide is added under nitrogen atmosphere and it is stirred for 1 hour at room temperature. The reaction mixture is added with stirring in 70 ml of ice water and the product is extracted with ethyl acetate. The organic phase is washed with 50 ml of water and dried on sodium sulfate. After chromatography of the crude product on silica gel with ethyl acetate/hexane as mobile solvent, 2.36 g (55.4% of theory) of 2α-iodo-1α-methylandrost-4-ene-3,17-dione is obtained as solid.

Workup

  1. additionThe reaction mixture is added
  2. extractionthe product is extracted with ethyl acetate
  3. washThe organic phase is washed with 50 ml of water
  4. customdried on sodium sulfate

Sources & evidence

ORD record
ord-f069c293454742eda539bb584c56e075
Source dataset
uspto-grants-1995_02
Patent number
US05391778

Reaction notes

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