Water → HCID 54289836, compound

HRID 1415850Notes

Reaction equation

HRID 1415850 reaction equation
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH:8]=[CH:9][C:10]4[C@:15]3([CH3:16])[CH:14]=[CH:13][C:12](=[O:20])[CH:11]=4)[C@@H:6]1[CH2:5][CH2:4][C:3]2=[O:21].[CH3:22][Al](C)C.O>O1CCOCC1.C1(C)C=CC=CC=1.[Cu]Br>[CH3:22][C@@H:14]1[C@@:15]2([CH3:16])[C:10]([CH:9]=[CH:8][C@@H:7]3[C@@H:17]2[CH2:18][CH2:19][C@@:2]2([CH3:1])[C@H:6]3[CH2:5][CH2:4][C:3]2=[O:21])=[CH:11][C:12](=[O:20])[CH2:13]1

Participants

7

Reactant 3

HCID 962WaterHCID 104880Androsta-1,4,6-triene-3,17-dioneHCID 16682925Trimethylaluminum

Product 1

HCID 54289836HCID 54289836, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
20 °C

Procedure

2.82 g (10 mmol) of androsta-1,4,6-triene-3,17-dione is dissolved in 20 ml of dioxane at 20° C. and mixed with 143.3 mg (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 stirred for 10 minutes at 20° C. For hydrolysis, 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, 2.97 g of 1α-methyl-androsta-4,6-diene-3,17-dione (99% of theory) of a melting point of 171° C. is obtained.

Workup

  1. additionis carefully added to the reaction
  2. stirringIt is stirred for 10 minutes more
  3. filtrationthe inorganic precipitate filtered off with dioxane
  4. washis washed again
  5. concentrationThe dioxane solution is concentrated by evaporation on a rotary evaporator
  6. customthe residue is chromatographed on silica gel with ethyl acetate/hexane as eluent
  7. concentrationAfter concentration
  8. customby evaporation of the fractions, 2.97 g of 1α-methyl-androsta-4,6-diene-3,17-dione (99% of theory) of a melting point of 171° C.
  9. customis obtained

Sources & evidence

ORD record
ord-ed917b12431d4c058e5845b148e7a72b
Source dataset
uspto-grants-1999_06
Patent number
US05908944

Reaction notes

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