Water → HCID 54302982, compound

HRID 1415851Notes

Reaction equation

HRID 1415851 reaction equation
[C:1]([O:4][CH:5]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:26])[C@H:11]3[CH2:12][CH:13]=[C:14]2[C:15](=[O:17])[CH3:16])[CH2:6]1)(=[O:3])[CH3:2].[CH3:27][Al](C)C.O>O1CCOCC1.C1(C)C=CC=CC=1.[Cu]Br>[C:1]([O:4][CH:5]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:26])[C@H:11]3[CH2:12][C@@H:13]([CH3:27])[C@@H:14]2[C:15](=[O:17])[CH3:16])[CH2:6]1)(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 962WaterHCID 109043983-Hydroxypregna-5,16-dien-20-one 3-acetateHCID 16682925Trimethylaluminum

Product 1

HCID 54302982HCID 54302982, compoundYield 30%

Reagents, catalysts & solvents 3

HCID 24593copper(I) bromideCatalystHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
20 °C

Procedure

3.56 g (10 mmol) of 3-acetoxy-pregna-5,16-dien-20-one is dissolved in 20 ml of dioxane at 20° C. and mixed with 143.3 g (1 mmol) of copper(I) bromide. 9.4 ml (11 mmol) of a 10% solution of trimethyl aluminum in toluene is added to the reaction at room temperature under nitrogen atmosphere and, after completion of the addition, stirred for 10 minutes at 20° C. For hydrolysis of the reaction solution, 1 ml of water dissolved in 5 ml of dioxane is carefully added to the reaction. It is stirred for 10 minutes more and the inorganic precipitate filtered off with dioxane is washed again. The dioxane solution is concentrated by evaporation on a rotary evaporator and the residue is chromatographed on silica gel with ethyl acetate/hexane as eluent. After concentration by evaporation of the fractions, 1.12 g of 3-acetoxy-16α-methyl-pregn-5-en-20-one (30% of theory) is obtained.

Workup

  1. additionafter completion of the addition
  2. additionis carefully added to the reaction
  3. stirringIt is stirred for 10 minutes more
  4. filtrationthe inorganic precipitate filtered off with dioxane
  5. washis washed again
  6. concentrationThe dioxane solution is concentrated by evaporation on a rotary evaporator
  7. customthe residue is chromatographed on silica gel with ethyl acetate/hexane as eluent
  8. concentrationAfter concentration
  9. customby evaporation of the fractions

Sources & evidence

ORD record
ord-e9e1e785a23c4a8d8209e44422037d65
Source dataset
uspto-grants-1999_06
Patent number
US05908944

Reaction notes

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