Potassium Bicarbonate → HCID 23251301, compound

HRID 1606483Notes

Reaction equation

HRID 1606483 reaction equation
C([O:4][C@@H:5]1[CH:24]=[CH:23][C@@:22]2([CH3:25])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:26])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C:15](=[O:17])[CH3:16])[CH2:6]1)(=O)C.C(O[C@@H]1[C@H](Br)C[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CC[C@@H]2C(=O)C)C1)(=O)C.C(=O)(O)[O-].[K+]>CO>[OH:4][C@@H:5]1[CH:24]=[CH:23][C@@:22]2([CH3:25])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:26])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C:15](=[O:17])[CH3:16])[CH2:6]1

Participants

5

Reactant 3

HCID 516893Potassium BicarbonateHCID 86733328HCID 86733328, compoundHCID 86733329HCID 86733329, compound

Product 1

HCID 23251301HCID 23251301, compoundYield 22.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of crude 3α-acetoxy-5α-pregn-1-en-20-one (4.0 g.) containing some 3α-acetoxy-2α-bromo-5α-pregnan-20-one, in dry methanol (120 ml.) was treated with potassium bicarbonate (4.5 g.), and the mixture was refluxed under nitrogen for 2 hours. The reaction mixture was concentrated in vacuo, then poured into water, and the product was extracted with methylene chloride. The extract was washed with water, dried (Na2SO4), and evaporated in vacuo. The residue (3.3 g.) was subjected to preparative layer chromatography. The more polar fraction, after crystallisation from methyl acetate, gave 3α-hydroxy-5α-pregn-1-en-20-one (780 mg), m.p. 150°-154°, [α]D + 28.9°. The less polar fraction after crystallisation from methyl acetate, gave 2α-bromo-3α-hydroxy-5α-pregnan-20-one (320 mg), m.p. 201°-204°, [α]D + 110.5°.

Workup

  1. temperaturethe mixture was refluxed under nitrogen for 2 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionpoured into water
  4. extractionthe product was extracted with methylene chloride
  5. washThe extract was washed with water
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo
  8. customThe more polar fraction, after crystallisation from methyl acetate

Sources & evidence

ORD record
ord-d67d19aee771446490a48a986b31db3f
Source dataset
uspto-grants-1976_04
Patent number
US03953429

Reaction notes

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