Acetic Acid → 17-Cyano-9,17-dihydroxyandrost-4-ene-3-one

HRID 1650075Notes

Reaction equation

HRID 1650075 reaction equation
C(O)(=[O:3])C.O[C@H:6]1[CH2:23][C@@:21]2([CH3:22])[C@@H:17]([CH2:18][CH2:19][C:20]2=O)[C@H:16]2[C@H:7]1[C@:8]1([CH3:27])[C:13]([C@@H:14](C)[CH2:15]2)=[CH:12]C(=O)[CH:10]=[CH:9]1.[C-:28]#[N:29].[K+].[OH2:31].[CH3:32][OH:33]>>[CH3:22][C@@:21]12[C:20]([OH:31])([C:28]#[N:29])[CH2:19][CH2:18][C@H:17]1[C@@H:16]1[CH2:15][CH2:14][C:13]3[C@@:8]([CH3:27])([C:7]1([OH:3])[CH2:6][CH2:23]2)[CH2:9][CH2:10][C:32](=[O:33])[CH:12]=3

Participants

6

Reactant 5

HCID 176Acetic Acid3×HCID 887MethanolHCID 962Water2×HCID 9032Potassium CyanideHCID 1508605911beta-Hydroxy-6alpha-methylandrosta-1,4-diene-3,17-dione

Product 1

HCID 308277817-Cyano-9,17-dihydroxyandrost-4-ene-3-one

Procedure

Glacial acetic acid (2.87 ml) is added to 9α-hydroxyandrost-4-ene-3,17-dione (0, 13.49 g) and potassium cyanide (4.98 g) slurried in methanol (45 ml) and stirred at 20°-25°. Glacial acetic acid (0.92 ml) is added followed by water (30 ml) over 13.7 hr via a syringe pump, keeping the mixture at 27°. The mixture is stirred an additional 2 hr at 27°. Additional glacial acetic acid (1.5 ml) is added at 15° followed by water (50 ml) at 10°. The mixture is stirred at 10° for 20 min and the product collected by vacuum filtration and washed with water. The solid is dried in an air stream for 24 hr to give the title compound, mp 229°-230°.

Workup

  1. customat 27°
  2. stirringThe mixture is stirred an additional 2 hr at 27°
  3. stirringThe mixture is stirred at 10° for 20 min
  4. filtrationthe product collected by vacuum filtration
  5. washwashed with water
  6. customThe solid is dried in an air stream for 24 hr

Sources & evidence

ORD record
ord-2fe352cd6628469e907ec94216c895ac
Source dataset
uspto-grants-1990_05
Patent number
US04921638

Reaction notes

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