Androstenedione → HCID 67830240, compound

HRID 1708900Notes

Reaction equation

HRID 1708900 reaction equation
C[C@]12CC[C@H]3[C@@H](CCC4[C@]3(C)CCC(=O)C=4)[C@@H]1CCC2=O.[C:22]([C:24]1([O:44][C:45](=[O:47])[CH3:46])[CH2:29][CH2:28][C@H:27]2[C@H:30]3[C@H:40]([CH2:41][CH2:42][C@:25]12[CH3:26])[C@:38]1([CH3:39])[C:33](=[CH:34][C:35](=[O:43])[CH2:36][CH2:37]1)[CH2:32][CH2:31]3)#[N:23]>CC(C)(O)C#N>[C:22]([C@@:24]1([O:44][C:45](=[O:47])[CH3:46])[CH2:29][CH2:28][C@H:27]2[C@H:30]3[C@H:40]([CH2:41][CH2:42][C@:25]12[CH3:26])[C@:38]1([CH3:39])[C:33](=[CH:34][C:35](=[O:43])[CH2:36][CH2:37]1)[CH2:32][CH2:31]3)#[N:23]

Participants

4

Reactant 2

HCID 6128AndrostenedioneHCID 57090946HCID 57090946, compound

Product 1

HCID 67830240HCID 67830240, compound

Reagents, catalysts & solvents 1

HCID 6406Acetone CyanohydrinSolvent

Procedure

4-Androsten-3,17-dione (20 g) is dissolved by gentle warming in acetone cyanohydrin (30 ml). The crystals which form after several minutes are filtered, washed with pentane, and then dissolved in a mixture of pyridine (50 ml) and acetic anhydride (50 ml). After 48 hours the volatiles are removed under reduced pressure. The residue is then dissolved in ether and washed successively with 5% hydrochloric acid and aqueous sodium bicarbonate. The organic solution is dried and concentrated to afford a mixture of C-17 epimers of 17-cyano-17-acetoxyandrost-4-ene-3-one. Chromatography affords 17β-cyano-17α-acetoxyandrost-4-ene-3-one.

Workup

  1. customThe crystals which form after several minutes
  2. filtrationare filtered
  3. washwashed with pentane
  4. dissolutiondissolved in a mixture of pyridine (50 ml) and acetic anhydride (50 ml)
  5. customAfter 48 hours the volatiles are removed under reduced pressure
  6. dissolutionThe residue is then dissolved in ether
  7. washwashed successively with 5% hydrochloric acid and aqueous sodium bicarbonate
  8. customThe organic solution is dried
  9. concentrationconcentrated
  10. customto afford

Sources & evidence

ORD record
ord-2075a849848249859298276cf144b94d
Source dataset
uspto-grants-1990_08
Patent number
US04946834

Reaction notes

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