Triethylamine → 11beta-Chloroacetoxy-3alpha-hydroxy-5alpha-pregnan-20-one

HRID 1701445Notes

Reaction equation

HRID 1701445 reaction equation
C(N(CC)CC)C.[Cl:8][CH2:9][C:10]([O:12][C@H:13]1[CH2:32][C@@:31]2([CH3:33])[C@@H:24]([CH2:25][CH2:26][C@@H:27]2[C:28](=[O:30])[CH3:29])[C@H:23]2[C@H:14]1[C@:15]1([CH3:35])[C@@H:20]([CH2:21][CH2:22]2)[CH2:19][C:18](=[O:34])[CH2:17][CH2:16]1)=[O:11]>O.O.Cl.Cl.Cl[Ir](Cl)(Cl)Cl>[Cl:8][CH2:9][C:10]([O:12][C@H:13]1[CH2:32][C@@:31]2([CH3:33])[C@@H:24]([CH2:25][CH2:26][C@@H:27]2[C:28](=[O:30])[CH3:29])[C@H:23]2[C@H:14]1[C@:15]1([CH3:35])[C@@H:20]([CH2:21][CH2:22]2)[CH2:19][C@H:18]([OH:34])[CH2:17][CH2:16]1)=[O:11]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 8673687011beta-Chloroacetoxy-5alpha-pregnane-3,20-dione

Product 1

HCID 8673686911beta-Chloroacetoxy-3alpha-hydroxy-5alpha-pregnan-20-oneYield 84.8%

Reagents, catalysts & solvents 2

HCID 16211483Tetrachloroiridium--hydrogen chloride--water (1/2/1)CatalystHCID 962WaterSolvent

Procedure

Chloroiridic acid reagent (10 ml) was neutralised to pH7 with triethylamine (1.1 ml), and to it was added 11β-chloroacetoxy-5α-pregnane-3,20-dione (880 mg). The solution was refluxed for 4 hours, and then cooled and diluted with water. The oily precipitate was extracted into ether/ethyl acetate, and the organic layer was washed with water, dried over sodium sulphate and evaporated to a yellow foam (875 mg) which was purified by preparative TLC in ethyl acetate/petrol (1/1) to give title compound (750 mg) as a white foam, [α]D +100° (c 0.62%).

Workup

  1. temperatureThe solution was refluxed for 4 hours
  2. temperaturecooled
  3. extractionThe oily precipitate was extracted into ether/ethyl acetate
  4. washthe organic layer was washed with water
  5. dry with materialdried over sodium sulphate
  6. customevaporated to a yellow foam (875 mg) which
  7. customwas purified by preparative TLC in ethyl acetate/petrol (1/1)

Sources & evidence

ORD record
ord-652fb85add6e4f3c9ee0e0c56791348d
Source dataset
uspto-grants-1980_03
Patent number
US04192871

Reaction notes

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