Water → 2-Imino-(25R)-5alpha-spirost-14-ene-3,12-dione

HRID 726169Notes

Reaction equation

HRID 726169 reaction equation
Br[CH:2]1[CH2:28][C@@:27]2([CH3:29])[C@@H:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:26]2[CH2:25][C:24](=[O:30])[C@@:23]2([CH3:31])[C:9]3=[CH:10][C@@H:11]3[O:16][C@@:15]4([O:22][CH2:21][C@H:19]([CH3:20])[CH2:18][CH2:17]4)[C@@H:13]([CH3:14])[C@@H:12]32)[CH2:4][C:3]1=[O:32].[N-:33]=[N+]=[N-].[Na+].[I-].[Na+].O>CN(C)C=O>[NH:33]=[C:2]1[CH2:28][C@@:27]2([CH3:29])[C@@H:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:26]2[CH2:25][C:24](=[O:30])[C@@:23]2([CH3:31])[C:9]3=[CH:10][C@@H:11]3[O:16][C@@:15]4([O:22][CH2:21][C@H:19]([CH3:20])[CH2:18][CH2:17]4)[C@@H:13]([CH3:14])[C@@H:12]32)[CH2:4][C:3]1=[O:32]

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 33557Sodium AzideHCID 15282201HCID 15282201, compound

Product 1

HCID 152822022-Imino-(25R)-5alpha-spirost-14-ene-3,12-dioneYield 93.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

500 mg (0.99 mmol) of 2-bromo-(25R)-5α-spirost-14-ene-3,12-dione (II) is dissolved in 50 ml of dimethylformamide. After adding 700 mg of sodium azide and a few milligrams of sodium iodide, the solution is stirred for 2 hours at 50° C. The reaction mixture is brought to room temperature, poured into 20 ml of water and extracted with methyl-tert-butyl ether. This extract is washed with saturated sodium chloride solution, dried on magnesium sulfate and concentrated by evaporation. After crystallization, 407 mg (80%) of iminoketone III is obtained.

Workup

  1. customis brought to room temperature
  2. extractionextracted with methyl-tert-butyl ether
  3. washThis extract is washed with saturated sodium chloride solution
  4. customdried on magnesium sulfate
  5. concentrationconcentrated by evaporation
  6. customAfter crystallization

Sources & evidence

ORD record
ord-1665762142dd4585b5357206ed3754cb
Source dataset
uspto-grants-1998_01
Patent number
US05708164

Reaction notes

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