Methane → Dehydroepiandrosterone

HRID 1824690Notes

Reaction equation

HRID 1824690 reaction equation
CC([O:4][CH:5]1[CH2:18][C:17]2[C:8]([CH3:24])([CH:9]3[CH:14]([CH2:15][CH:16]=2)[CH:13]2[CH2:19][CH2:20][C:21](=[O:22])[C:12]2([CH3:23])[CH2:11][CH2:10]3)[CH2:7][CH2:6]1)=O.C(=O)([O-])[O-].[K+].[K+].C>CO>[CH3:23][C@@:12]12[C:21](=[O:22])[CH2:20][CH2:19][C@H:13]1[C@@H:14]1[CH2:15][CH:16]=[C:17]3[CH2:18][C@@H:5]([OH:4])[CH2:6][CH2:7][C@:8]3([CH3:24])[C@H:9]1[CH2:10][CH2:11]2

Participants

5

Reactant 3

HCID 297MethaneHCID 11430Potassium CarbonateHCID 540877HCID 540877, compound

Product 1

HCID 5881Dehydroepiandrosterone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
15 °C

Procedure

DHEA was prepared from DHEA acetate (obtained from Diosynth, Chicago, Ill. or Berlichem, Montville, N.J.) by saponification using potassium carbonate in methanol. The product was dissolved in 6 parts methanol at reflux, and charcoal was added and removed by filtration. The methanol was evaporated until a volume of 3 parts remained, and the solution was cooled to 15° C., maintained at this temperature for 1 hour, and filtered. The wet product was refluxed with 8.5 parts of water to remove the methanol, filtered, and dried under vacuum at 90° C. The loss on drying specification for the final product was ≦0.5%, and the specification for residual methanol was ≦0.01%.

Workup

  1. temperatureat reflux
  2. customremoved by filtration
  3. customThe methanol was evaporated until a volume of 3 parts
  4. temperaturemaintained at this temperature for 1 hour
  5. filtrationfiltered
  6. temperatureThe wet product was refluxed with 8.5 parts of water
  7. customto remove the methanol
  8. filtrationfiltered
  9. customdried under vacuum at 90° C
  10. dry with materialThe loss on drying specification for the final product

Sources & evidence

ORD record
ord-6ddea3d788d249cda889f630f537ac44
Source dataset
uspto-grants-2006_05
Patent number
US07045513B1

Reaction notes

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