Sodium Carbonate → 17beta,19-Dihydroxy-1alpha-methyl-5alpha-androstan-3-one

HRID 1834966Notes

Reaction equation

HRID 1834966 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@H:21]([CH2:22][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@H:21]([CH2:22][C:23](=[O:33])[CH2:24][C@@H:25]1[CH3:32])[CH2:20][CH2:19]3

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 8673542517beta,19-Dihydroxy-1alpha-methyl-5alpha-androstan-3-one dipropionate

Product 1

HCID 7061509617beta,19-Dihydroxy-1alpha-methyl-5alpha-androstan-3-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 17β,19-dihydroxy-1α-methyl-5α-androstan-3-one dipropionate in methanol is refluxed for two hours with aqueous sodium carbonate. The methanol is removed under vacuum and water added to the residue. Crystallization of the solid residue from an acetone-hexane solution yields pure 17β,19-dihydroxy-1α-methyl-5α-androstan-3-one.

Workup

  1. customThe methanol is removed under vacuum and water
  2. additionadded to the residue
  3. customCrystallization of the solid residue from an acetone-hexane solution

Sources & evidence

ORD record
ord-d04e4e0a71514b40b1be37c5d4208fb2
Source dataset
uspto-grants-1978_01
Patent number
US04071625

Reaction notes

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