21-Methyl-5alpha-pregnane-3,11,20-trione → 3alpha-Hydroxy-21-methyl-5alpha-pregnane-11,20-dione

HRID 1973715Notes

Reaction equation

HRID 1973715 reaction equation
[CH3:1][CH2:2][C:3](=[O:25])[C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([C:19](=[O:23])[CH2:20]2)[C@:16]2([CH3:17])[C@H:11]([CH2:12][C:13](=[O:24])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1>O.Cl.Cl.Cl[Ir](Cl)(Cl)Cl>[OH:24][C@@H:13]1[CH2:14][CH2:15][C@@:16]2([CH3:17])[C@@H:11]([CH2:10][CH2:9][C@@H:8]3[C@@H:18]2[C:19](=[O:23])[CH2:20][C@@:21]2([CH3:22])[C@H:7]3[CH2:6][CH2:5][C@@H:4]2[C:3](=[O:25])[CH2:2][CH3:1])[CH2:12]1

Participants

3

Reactant 1

HCID 13171057521-Methyl-5alpha-pregnane-3,11,20-trione

Product 1

HCID 867342873alpha-Hydroxy-21-methyl-5alpha-pregnane-11,20-dione

Reagents, catalysts & solvents 1

HCID 16211483Tetrachloroiridium--hydrogen chloride--water (1/2/1)Catalyst

Procedure

21-Methyl-5α-pregnane-3,11,20-trione (0.4 g.) was added to "stock" chloroiridic acid solution (75 ml.) and the resulting mixture was refluxed for 2 hr. The solution was then cooled and partitioned between water and ether. The organic layer was washed with saturated aqueous sodium bicarbonate, dried (Na2SO4) and evaporated.

Workup

  1. temperaturethe resulting mixture was refluxed for 2 hr
  2. temperatureThe solution was then cooled
  3. custompartitioned between water and ether
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-74f27b354f7046d6a5fd64635496c2cf
Source dataset
uspto-grants-1976_12
Patent number
US03998829

Reaction notes

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