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

HRID 1834909Notes

Reaction equation

HRID 1834909 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 86735421HCID 86735421, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 17α,19-dihydroxy-1α-methyl-4-androsten-3-one dipropionate in methanol is refluxed for about two hours with aqueous sodium carbonate. The solvent is removed and the residue dissolved in chloroform. The chloroform extract is washed well with water, dried over magnesium sulfate and evaporated under vacuum. The residue which remains is 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. extractionThe chloroform extract
  4. washis washed well with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under vacuum
  7. customThe residue which remains is crystallized from acetonitrile

Sources & evidence

ORD record
ord-f0b39c10a9ec45fd9e87dfca705dc44a
Source dataset
uspto-grants-1978_01
Patent number
US04071624

Reaction notes

Loading…