Water → (1alpha,5alpha,17beta)-17-(Acetyloxy)-1-methylandrostan-3-one

HRID 1415860Notes

Reaction equation

HRID 1415860 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:24])[CH:17]=[CH:18]1)[CH2:13][CH2:12]3)(=[O:3])[CH3:2].O.[C:26](OCC)(=O)C>>[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:24])[CH2:17][C@@H:18]1[CH3:26])[CH2:13][CH2:12]3)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 30346553-Oxoandrost-1-en-17-yl acetate

Product 1

HCID 107497(1alpha,5alpha,17beta)-17-(Acetyloxy)-1-methylandrostan-3-one

Conditions

Temperature
25 °C

Procedure

3.3 g (10 mmol) of 17β-acetoxy-5α-androst-1-en-3-one in 15 ml of ethyl acetate and 143 mg (0.1 mmol) of CuBr are added to solution a). It is stirred for 16 hours at 25° C. The reaction solution is hydrolyzed with 1 ml of water, stirred for 15 minutes more and the inorganic solid is filtered off. The solid is washed with ethyl acetate. After evaporation of the solvent, 3.5 g of substance is obtained that is recrystallized from acetone. After suctioning off of the crystals, 2.9 g of 17-acetoxy-1α-methyl-5α-androstan-3-one of a melting point of 179-180° C. is obtained.

Workup

  1. stirringstirred for 15 minutes more
  2. filtrationthe inorganic solid is filtered off
  3. washThe solid is washed with ethyl acetate
  4. customAfter evaporation of the solvent, 3.5 g of substance
  5. customis obtained
  6. customthat is recrystallized from acetone
  7. customis obtained

Sources & evidence

ORD record
ord-527d051b762e480aa03277a427af04fa
Source dataset
uspto-grants-1999_06
Patent number
US05908944

Reaction notes

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