1beta,2beta-Methylene-19-tetrahydropyranyloxy-5-androstene-3beta,17beta-diol → 19-Hydroxy-1beta,2beta-methylene-4-androstene-3,17-dione

HRID 1390739Notes

Reaction equation

HRID 1390739 reaction equation
[CH2:1]1[C@@H:3]2[C@H:4]([OH:29])[CH2:5][C:6]3[C@:19]([CH2:20][O:21]C4CCCCO4)([C@H:2]12)[C@@H:18]1[C@H:9]([C@H:10]2[C@@:14]([CH2:16][CH2:17]1)([CH3:15])[C@@H:13]([OH:28])[CH2:12][CH2:11]2)[CH2:8][CH:7]=3.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[OH:21][CH2:20][C@@:19]12[C@@H:18]3[C@H:9]([C@H:10]4[C@@:14]([CH2:16][CH2:17]3)([CH3:15])[C:13](=[O:28])[CH2:12][CH2:11]4)[CH2:8][CH2:7][C:6]1=[CH:5][C:4](=[O:29])[C@H:3]1[CH2:1][C@@H:2]21

Participants

4

Reactant 2

HCID 706050941beta,2beta-Methylene-19-tetrahydropyranyloxy-5-androstene-3beta,17beta-diolHCID 131709961Jones' reagent

Product 1

HCID 7060589619-Hydroxy-1beta,2beta-methylene-4-androstene-3,17-dione

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The 1β,2β-methylene-19-tetrahydropyranyloxy-5-androstene-3β,17β-diol is dissolved in acetone and Jones Reagent added until a persistent yellow-orange color appears. After stirring at room temperature for 10 minutes the mixture is poured onto ice water and the precipitate which forms is collected by filtration. This precipitate is dissolved in a solution of hydrochloric acid in aqueous methanol and stirred for 30 minutes at room temperature. The methanol is removed by evaporation and the residue is triturated with water. The solid which results is filtered and crystallized from an acetone solution to yield 19-hydroxy-1β,2β-methylene-4-androstene-3,17-dione.

Workup

  1. additionis poured onto ice water
  2. filtrationthe precipitate which forms is collected by filtration
  3. dissolutionThis precipitate is dissolved in a solution of hydrochloric acid in aqueous methanol
  4. stirringstirred for 30 minutes at room temperature
  5. customThe methanol is removed by evaporation
  6. customthe residue is triturated with water
  7. customThe solid which results
  8. filtrationis filtered
  9. customcrystallized from an acetone solution

Sources & evidence

ORD record
ord-64e47cf0e4c849a2adf26cd81b206509
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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