Sodium Azide → HCID 13714632, compound

HRID 845211Notes

Reaction equation

HRID 845211 reaction equation
Br[C@H:2]1[C:19]2[C@:14]([CH3:21])([CH:15]=[CH:16][C:17](=[O:20])[CH:18]=2)[C@@H:13]2[C@H:4]([C@H:5]3[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C:8](=[O:22])[CH2:7][CH2:6]3)[C@@H:3]1OC(=O)C.[N-:27]=[N+:28]=[N-:29].[Na+]>CN(C)C=O.O>[N:27]([C:18]1[C:17](=[O:20])[CH:16]=[CH:15][C@@:14]2([CH3:21])[C:19]=1[CH:2]=[CH:3][C@@H:4]1[C@@H:13]2[CH2:12][CH2:11][C@@:9]2([CH3:10])[C@H:5]1[CH2:6][CH2:7][C:8]2=[O:22])=[N+:28]=[N-:29]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 57200242HCID 57200242, compound

Product 1

HCID 13714632HCID 13714632, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 0.5 g of 6β-bromo-7α-acetoxyandrosta-1,4-dien-3,17-dione in 30 ml of dimethylformamide and 1.2 ml of water are added 0.11 g of sodium azide. The reaction mixture is heated at 100° C. for 45 minutes, cooled, poured into 500 ml of iced water and extracted with ethyl acetate. The combined extracts are washed with water, dried over sodium sulphate, filtered and evaporated in vacuo to give a residue which is purified by column chromatography on silica gel. Elution with n-hexane:ethyl acetate 70:30 yields 0.28 g of the title compound, m.p. 123°-125° C. (dec.);

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts are washed with water
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give a residue which
  8. customis purified by column chromatography on silica gel
  9. washElution with n-hexane:ethyl acetate 70:30

Sources & evidence

ORD record
ord-1730e077afc1435ba289687f2068d1ea
Source dataset
uspto-grants-1988_07
Patent number
US04757061

Reaction notes

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