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

HRID 918059Notes

Reaction equation

HRID 918059 reaction equation
[Cl:1][CH2:2][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>O.Cl.Cl.Cl[Ir](Cl)(Cl)Cl>[Cl:1][CH2:2][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

Participants

3

Reactant 1

HCID 2279148521-(3'-Chloropropoxy)-5alpha-pregnane-3,11,20-trione

Product 1

HCID 2279148421-(3'-Chloropropoxy)-3alpha-hydroxy-5alpha-pregnane-11,20-dioneYield 48.9%

Reagents, catalysts & solvents 1

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

Procedure

The less polar residue, crude 21-(3'-chloropropoxy)-5α-pregnane-3,11,20-trione (1.1 g.) was treated with `stock` chloroiridic acid solution. The mixture was then refluxed for 24 hours, cooled and partitioned between water and ether. The organic layer was washed with water, dried (Na2SO4) and evaporated. The residue was subjected to preparative t.l.c. EtOAc/petrol 1:1 to give title compound (0.54 g.) as a white foam, [α]D + 73° (c 1.3).

Workup

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

Sources & evidence

ORD record
ord-597d44c9671e4854969dedbacdbf017a
Source dataset
uspto-grants-1976_07
Patent number
US03969345

Reaction notes

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