Androstenedione → HCID 67830240, compound

HRID 1494675Notes

Reaction equation

HRID 1494675 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-20c4a82b8b734aa4a39a2d9bc968f4e6
Source dataset
uspto-grants-1991_06
Patent number
US05026882

Reaction notes

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