Sodium Azide → HCID 13714628, compound

HRID 845208Notes

Reaction equation

HRID 845208 reaction equation
CS(O[C:6]1[C:23](=[O:24])[CH2:22][CH2:21][C@@:20]2([CH3:25])[C:7]=1[CH2:8][CH2:9][C@@H:10]1[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]1[CH2:12][CH2:13][C:14]2=[O:26])(=O)=O.[N-:27]=[N+:28]=[N-:29].[Na+]>CN(C)C=O.O>[N:27]([C:6]1[C:23](=[O:24])[CH2:22][CH2:21][C@@:20]2([CH3:25])[C:7]=1[CH2:8][CH2:9][C@@H:10]1[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]1[CH2:12][CH2:13][C:14]2=[O:26])=[N+:28]=[N-:29]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 13714624HCID 13714624, compound

Product 1

HCID 13714628HCID 13714628, compoundYield 60.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 1.0 g of 4-methanesulfonyloxyandrost-4-en-3,17-dione in 5 ml of dimethylformamide are added 220 mg of powdered sodium azide dissolved in 3 ml of water. The resulting mixture is heated at 60° C. for 1 hour, cooled, poured into 250 ml of cold water and extracted with ethyl acetate (4×50 ml). The combined extracts are washed with saturated NaCl aqueous solution, dried over Na2SO4 and evaporated in vacuo to yield a residue which is purified by flash column chromatography on neutral Al2O3. Elution with n-hexane:diethyl ether 1:1 gives 0.52 g of the title compound, m.p. 142°-143° C.

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate (4×50 ml)
  3. washThe combined extracts are washed with saturated NaCl aqueous solution
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo
  6. customto yield a residue which
  7. customis purified by flash column chromatography on neutral Al2O3
  8. washElution with n-hexane:diethyl ether 1:1

Sources & evidence

ORD record
ord-2d3240cab8884db78bf8d1939b67f3fd
Source dataset
uspto-grants-1988_07
Patent number
US04757061

Reaction notes

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