Potassium Bicarbonate → Deoxycorticosterone

HRID 979421Notes

Reaction equation

HRID 979421 reaction equation
C(=O)([O-])O.[K+].C([O:14][CH2:15][C:16](=[O:37])[C@@H:17]1[C@:34]2([CH3:35])[C@H:20]([C@H:21]3[C@H:31]([CH2:32][CH2:33]2)[C@:29]2([CH3:30])[C:24](=[CH:25][C:26](=[O:36])[CH2:27][CH2:28]2)[CH2:23][CH2:22]3)[CH2:19][CH2:18]1)(=O)C1C=CC=CC=1>O.CO.C(O)C>[CH2:15]([OH:14])[C:16](=[O:37])[C@@H:17]1[C@:34]2([CH3:35])[C@H:20]([C@H:21]3[C@H:31]([CH2:32][CH2:33]2)[C@:29]2([CH3:30])[C:24](=[CH:25][C:26](=[O:36])[CH2:27][CH2:28]2)[CH2:23][CH2:22]3)[CH2:19][CH2:18]1

Participants

6

Reactant 2

HCID 516893Potassium BicarbonateHCID 156740314-Pregnene-3,20-dione-21-ol benzoate

Product 1

HCID 6166DeoxycorticosteroneYield 100.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution containing 7.5 g of potassium hydrogen carbonate in 14 ml of water is added to the suspension containing 2.5 g (5.7 mmoles) of 4-pregnene-3,20-dione-21-ol benzoate in 100 ml of methanol and the mixture is refluxed for 3 hours. Subsequently, the solvent is evaporated and the residue is taken up in 150 ml of water. The product is extracted 3 times with 80 ml of ethyl acetate each, the organic phase is washed with water, dried and evaporated. The residue is recrystallized from a mixture of ethyl acetate and diisopropyl ether to give 1.89 g 99% yield of the aimed product, m.p.: 132°-135° C., [α]D =+175.2° (c=0.5 in ethanol).

Workup

  1. additionis added to the suspension
  2. temperaturethe mixture is refluxed for 3 hours
  3. customSubsequently, the solvent is evaporated
  4. extractionThe product is extracted 3 times with 80 ml of ethyl acetate each, the organic phase
  5. washis washed with water
  6. customdried
  7. customevaporated
  8. customThe residue is recrystallized from a mixture of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-1dd3e54e73484157b845fea3957245fe
Source dataset
uspto-grants-1987_05
Patent number
US04668437

Reaction notes

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