Sulfuric Acid → (17alpha)-17-Hydroxy-3-oxoandrosta-4,9(11)-diene-17-carbonitrile

HRID 1650074Notes

Reaction equation

HRID 1650074 reaction equation
[CH3:1][C@@:2]12[C:10]([OH:13])([C:11]#[N:12])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:14][CH2:15][C:16]3[C@@:22]([CH3:23])([C:5]1(O)[CH2:4][CH2:3]2)[CH2:21][CH2:20][C:18](=[O:19])[CH:17]=3.S(=O)(=O)(O)O>O>[C:11]([C@@:10]1([OH:13])[CH2:9][CH2:8][C@H:7]2[C@H:6]3[C:5](=[CH:4][CH2:3][C@:2]12[CH3:1])[C@:22]1([CH3:23])[C:16](=[CH:17][C:18](=[O:19])[CH2:20][CH2:21]1)[CH2:15][CH2:14]3)#[N:12]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 308277817-Cyano-9,17-dihydroxyandrost-4-ene-3-one

Product 1

HCID 10859900(17alpha)-17-Hydroxy-3-oxoandrosta-4,9(11)-diene-17-carbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

17β-Cyano-9α,17α-dihydroxyandrost-4-en-3-one (I, EXAMPLE 85, 313 mg) is added to sulfuric acid (57%, 5 ml) at 2° and is stirred at 2°-5° for several hr and then overnight at 22°; solids formed. Water (10 ml) is added at 10°, the mixture stirred for 15 min, the solids collected and air dried to give the title compound, NMR (CDCl3 /DMSO-d6 ; 5/1) 5.7, 5.6, 1.4 and 0.9 δ.

Workup

  1. customovernight
  2. customat 22°
  3. customsolids formed
  4. stirringthe mixture stirred for 15 min
  5. customthe solids collected
  6. customair dried

Sources & evidence

ORD record
ord-8a7407084025441487b5cfe4085f2b7c
Source dataset
uspto-grants-1990_05
Patent number
US04921638

Reaction notes

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