21-(2'-Cyanoethoxy)-5alpha-pregnane-3,11,20-trione → 21-(2'-Cyanoethoxy)-3alpha-hydroxy-5alpha-pregnane-11,20-dione

HRID 918058Notes

Reaction equation

HRID 918058 reaction equation
[C:1]([CH2:3][CH2:4][O:5][CH2:6][C:7](=[O:29])[C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([C:23](=[O:27])[CH2:24]2)[C@:20]2([CH3:21])[C@H:15]([CH2:16][C:17](=[O:28])[CH2:18][CH2:19]2)[CH2:14][CH2:13]3)[CH2:10][CH2:9]1)#[N:2]>O.Cl.Cl.Cl[Ir](Cl)(Cl)Cl>[C:1]([CH2:3][CH2:4][O:5][CH2:6][C:7](=[O:29])[C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([C:23](=[O:27])[CH2:24]2)[C@:20]2([CH3:21])[C@H:15]([CH2:16][C@H:17]([OH:28])[CH2:18][CH2:19]2)[CH2:14][CH2:13]3)[CH2:10][CH2:9]1)#[N:2]

Participants

3

Reactant 1

HCID 2279148021-(2'-Cyanoethoxy)-5alpha-pregnane-3,11,20-trione

Product 1

HCID 2279147921-(2'-Cyanoethoxy)-3alpha-hydroxy-5alpha-pregnane-11,20-dioneYield 0.2%

Reagents, catalysts & solvents 1

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

Procedure

The product, crude 21-(2'-cyanoethoxy)-5α-pregnane-3,11,20-trione (0;80 g.) was treated with chloroiridic acid solution (24 ml.). The mixture was refluxed for 24 hours cooled and partitioned between water and ether. The organic layer was washed with saturated aqueous sodium bicarbonate, water, dried (Na2SO4) and evaporated. The residue was subjected to preparative t.l.c. EtOAc, petrol (1:1) to give title compound (0.2 g.) as a white foam, [α]D + 85° (c 1.1).

Workup

  1. temperatureThe mixture was refluxed for 24 hours
  2. temperaturecooled
  3. custompartitioned between water and ether
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate, water
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-4b63a3f388e649d4be7738fa6366b288
Source dataset
uspto-grants-1976_07
Patent number
US03969345

Reaction notes

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