Water → HCID 67557511, compound

HRID 1415857Notes

Reaction equation

HRID 1415857 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@H:14]([CH2:15][C:16](=[O:25])[C:17]([Br:24])=[CH:18]1)[CH2:13][CH2:12]3)(=[O:3])[CH3:2].[CH3:26][Al](C)C.O>C(OCC)(=O)C.C1(C)C=CC=CC=1>[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@H:14]([CH2:15][C:16](=[O:25])[C@H:17]([Br:24])[C@@H:18]1[CH3:26])[CH2:13][CH2:12]3)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 16682925TrimethylaluminumHCID 67557463HCID 67557463, compound

Product 1

HCID 67557511HCID 67557511, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

14.3 mg (0.1 mmol) of CuBr is added at room temperature to 818 mg (2 mmol) of 17β-acetoxy-2-bromo-5α-androst-1-en-3-one (produced according to J. Org. Chem. 1982, 47, 5090; from 17β-acetoxy-2-brom-5α-androst-1-en-3-one) in 4 ml of ethyl acetate. 1.9 ml (2.2 mmol) of a 10% solution of trimethyl aluminum in toluene is instilled at room temperature. It is stirred at room temperature for 45 minutes. For hydrolysis, 0.18 ml of water is added, the solid is suctioned off and washed again with ethyl acetate. The solution is concentrated by evaporation and the residue is chromatographed on silica gel with hexane/ethyl acetate as eluent. After concentration by evaporation of the chromatography fractions, 600 mg of 17β-acetoxy-2α-bromo-1α-methyl-5α-androstan-3-one is obtained.

Workup

  1. customis instilled at room temperature
  2. additionis added
  3. washwashed again with ethyl acetate
  4. concentrationThe solution is concentrated by evaporation
  5. customthe residue is chromatographed on silica gel with hexane/ethyl acetate as eluent
  6. concentrationAfter concentration
  7. customby evaporation of the chromatography fractions

Sources & evidence

ORD record
ord-2595afdd97194a18a9170044d59c5d45
Source dataset
uspto-grants-1999_06
Patent number
US05908944

Reaction notes

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