Acetone Cyanohydrin → 17-Cyano-9,17-dihydroxyandrost-4-ene-3-one

HRID 1650073Notes

Reaction equation

HRID 1650073 reaction equation
CC(C)(O)[C:3]#[N:4].[OH:7][C@:8]12[CH2:25][CH2:24][C@@:22]3([CH3:23])[C@@H:18]([CH2:19][CH2:20][C:21]3=[O:26])[C@@H:17]1[CH2:16][CH2:15][C:14]1[C@:9]2([CH3:28])[CH2:10][CH2:11][C:12](=[O:27])[CH:13]=1.[C-]#N.[K+]>CO>[CH3:23][C@@:22]12[C:21]([OH:26])([C:3]#[N:4])[CH2:20][CH2:19][C@H:18]1[C@@H:17]1[CH2:16][CH2:15][C:14]3[C@@:9]([CH3:28])([C:8]1([OH:7])[CH2:25][CH2:24]2)[CH2:10][CH2:11][C:12](=[O:27])[CH:13]=3

Participants

5

Reactant 3

HCID 6406Acetone CyanohydrinHCID 9032Potassium CyanideHCID 104250179alpha-Hydroxyandrost-4-ene-3,17-dione

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetone cyanohydrin (1.37 ml) is added to a mixture of 9α-hydroxyandrost-4-ene-3,17-dione (0, U.S. Pat. No. 3,065,146, 3.024 g) in methanol (10 ml). The mixture is stirred at about 35°-39° for about 2 hr, then at about 4°-54° for 1.25 hr. 0.1 ml of a potassium cyanide solution (1 g in 2.0 ml of water) is added and the mixture stirred at about 50°-55° for 30 min and then allowed to stand at 20°-25° overnight. The solids are collected, washed well with methanol and dried under reduced pressure at about 55° for 3 hr to give the title compound, NMR (CDCl3 /DMSO-d6 ; 10/1) 5.8, 2.4, 1.3 and 1.0 δ.

Workup

  1. waitat about 4°-54° for 1.25 hr
  2. stirringthe mixture stirred at about 50°-55° for 30 min
  3. waitto stand at 20°-25° overnight
  4. customThe solids are collected
  5. washwashed well with methanol
  6. customdried under reduced pressure at about 55° for 3 hr

Sources & evidence

ORD record
ord-fb6ff67090e045d793cbe38de9323856
Source dataset
uspto-grants-1990_05
Patent number
US04921638

Reaction notes

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