1,3-Dibromo-5,5-dimethylhydantoin → 2alpha-Bromo-1alpha-methyl-4-androstene-3,17-dione

HRID 2350830Notes

Reaction equation

HRID 2350830 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.[Br:26]N1C(C)(C)C(=O)N(Br)C1=O>O1CCOCC1.O>[Br: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

5

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 108716113-Acetoxy-1alpha-methylandrosta-2,4-dien-17-one

Product 1

HCID 678940762alpha-Bromo-1alpha-methyl-4-androstene-3,17-dioneYield 193.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Under ice cooling, a suspension of 5.18 g of 3-acetoxy-1α-methylandrosta-2,4-dien-17-one in 50 ml of dioxane and 100 ml of water is combined in portions with 2.2 g of 1,3-dibromo-5,5-dimethylhydantoin and stirred for one hour at room temperature. Subsequently, the mixture is precipitated into 1 liter of water saturated with sodium chloride, 2.7 g of sodium sulfite is added, and the mixture is stirred for 60 minutes. The precipitated residue is filtered off, washed free of chloride with water, and dried, thus obtaining 5.65 g of a mixture of 2β-bromo-1α-methyl-4-androstene-3,17-dione and 2β-bromo-1α-methyl-4-androstene-3,17-dione.

Workup

  1. customSubsequently, the mixture is precipitated into 1 liter of water saturated with sodium chloride, 2.7 g of sodium sulfite
  2. additionis added
  3. stirringthe mixture is stirred for 60 minutes
  4. filtrationThe precipitated residue is filtered off
  5. washwashed free of chloride with water
  6. customdried

Sources & evidence

ORD record
ord-5680ed06500f4010922791662f3f4af9
Source dataset
uspto-grants-1989_10
Patent number
US04871482

Reaction notes

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