Sodium Carbonate → 17beta,19-Dihydroxy-1alphamethyl-4-androsten-3-one

HRID 371839Notes

Reaction equation

HRID 371839 reaction equation
C(O)(=O)CC.C(O)(=O)CC.[OH:11][C@H:12]1[CH2:17][CH2:16][C@H:15]2[C@H:18]3[C@H:29]([CH2:30][CH2:31][C@:13]12[CH3:14])[C@:26]1([CH2:27][OH:28])[C:21](=[CH:22][C:23](=[O:33])[CH2:24][C@@H:25]1[CH3:32])[CH2:20][CH2:19]3.C(=O)([O-])[O-].[Na+].[Na+]>CO>[OH:11][C@H:12]1[CH2:17][CH2:16][C@H:15]2[C@H:18]3[C@H:29]([CH2:30][CH2:31][C@:13]12[CH3:14])[C@:26]1([CH2:27][OH:28])[C:21](=[CH:22][C:23](=[O:33])[CH2:24][C@@H:25]1[CH3:32])[CH2:20][CH2:19]3

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 8673472917beta,19-Dihydroxy-1alpha-methyl-4-androsten-3-one dipropionate

Product 1

HCID 2279742517beta,19-Dihydroxy-1alphamethyl-4-androsten-3-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 17β,19-dihydroxy-1α-methyl-4-androsten-3-one dipropionate in methanol is refluxed for two hours with aqueous sodium carbonate. The solvent is removed and the residue dissolved in chloroform. The chloroform solution is washed well with water, dried over magnesium sulfate and evaporated under vacuum. The residue which remains in crystallized from acetonitrile to yield 17β,19-dihydroxy-1α-methyl-4-androsten-3-one.

Workup

  1. customThe solvent is removed
  2. dissolutionthe residue dissolved in chloroform
  3. washThe chloroform solution is washed well with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under vacuum
  6. customin crystallized from acetonitrile

Sources & evidence

ORD record
ord-f8042fc939c3450a8463ef2ff819279b
Source dataset
uspto-grants-1978_05
Patent number
US04087524

Reaction notes

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