Methanol → 7beta-Hydroxydehydroepiandrosterone

HRID 1753114Notes

Reaction equation

HRID 1753114 reaction equation
CO.C([O:6][C@H:7]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C:9](=[CH:10][C@H:11]([OH:27])[C@@H:12]3[C@@H:21]2[CH2:20][CH2:19][C@@:17]2([CH3:18])[C@H:13]3[CH2:14][CH2:15][C:16]2=[O:26])[CH2:8]1)(=O)C.C([O-])([O-])=O.[Na+].[Na+]>O>[CH3:18][C@:17]12[CH2:19][CH2:20][C@H:21]3[C@@H:12]([C@@H:11]([OH:27])[CH:10]=[C:9]4[C@:22]3([CH3:25])[CH2:23][CH2:24][C@H:7]([OH:6])[CH2:8]4)[C@@H:13]1[CH2:14][CH2:15][C:16]2=[O:26]

Participants

5

Reactant 3

HCID 887MethanolHCID 10340Sodium CarbonateHCID 11302419HCID 11302419, compound

Product 1

HCID 98179547beta-HydroxydehydroepiandrosteroneYield 67.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 500 L reactor was charged 230 kg methanol, 33 kg (wet) 3β-acetoxy-7β-hydroxy-5-androsten-17-one, 108 kg water and 15 kg Na2CO3. The mixture was heated to reflux for 3 hours. Methanol was removed under vacuum whereupon 250 kg of water was added to the residue. The mixture was put in refrigerator overnight to give a precipitate. The solids were collected by filtration, then washed with water and dried at 40-50° C. to yield 9.5-10.5 kg (67.9-75.0%) of the title compound as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours
  3. customMethanol was removed under vacuum whereupon 250 kg of water
  4. additionwas added to the residue
  5. customwas put in refrigerator overnight
  6. customto give a precipitate
  7. filtrationThe solids were collected by filtration
  8. washwashed with water
  9. customdried at 40-50° C.

Sources & evidence

ORD record
ord-168f9c242cb84400871392658d604c74
Source dataset
uspto-grants-2015_10
Patent number
US09163059B2

Reaction notes

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