Sodium Thiosulfate → 2beta-Iodo-1alpha-methylandrost-4-ene-3,17-dione

HRID 275065Notes

Reaction equation

HRID 275065 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.C([O-])(=O)C.[Na+].[I:31]Cl.S([O-])([O-])(=O)=S.[Na+].[Na+]>CC(C)=O.C(OCC)(=O)C.CCCCCC>[I:31][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

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 24640Iodine chlorideHCID 517045Sodium AcetateHCID 108716113-Acetoxy-1alpha-methylandrosta-2,4-dien-17-one

Product 1

HCID 111443782beta-Iodo-1alpha-methylandrost-4-ene-3,17-dione

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
-10 °C

Procedure

68.95 g of 88.8% (0.179 mol) 3-acetoxy-1α-methyl-androsta-2,4-dien-17-one (DE-A 3715869) is dissolved in 800 ml of acetone, mixed with 32.9 g (0.4 mol) of anhydrous sodium acetate and cooled with stirring to -10° C. Then, 29 g (0.179 mol) of iodine chloride (iodine monochloride) is added under nitrogen atmosphere at -10° C. and it is stirred for another 30 minutes. Then, it is added to 6 l of ice water mixed with 6.65 g of sodium thiosulfate, the product is extracted with ethyl acetate, the organic phase is dried on sodium sulfate, filtered and concentrated by evaporation up to 200 ml. After standing overnight, the precipitated solid is suctioned off and dried. 49 g (64% of theory) of product is obtained. After chromatography of the mother liquor on silica gel with ethyl acetate/hexane as mobile solvent, another 10 g (13% of theory) of the title compound is obtained. The total yield is 59 g (77% of theory) of 2β-iodo-1α-methylandrost-4-ene-3,17-dione.

Workup

  1. temperaturecooled
  2. stirringit is stirred for another 30 minutes
  3. extractionthe product is extracted with ethyl acetate
  4. customthe organic phase is dried on sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation up to 200 ml
  7. customdried
  8. custom49 g (64% of theory) of product is obtained

Sources & evidence

ORD record
ord-675206d2f86b4e3d9ce558f31f8b3106
Source dataset
uspto-grants-1995_02
Patent number
US05391778

Reaction notes

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