1,4-Diiodobutane → (4aRS,5SR,8aRS)-1-benzyl-5-(pyrrolidin-1-yl)perhydroquinoxaline-2,3-dione

HRID 1876800

Reaction equation

HRID 1876800 reaction equation
[NH2:1][CH:2]1[CH2:11][CH2:10][CH2:9][CH:8]2[CH:3]1[NH:4][C:5](=[O:20])[C:6](=[O:19])[N:7]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])(O)=O.[Na+].I[CH2:27][CH2:28][CH2:29][CH2:30]I>CC#N>[CH2:12]([N:7]1[CH:8]2[CH:3]([CH:2]([N:1]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[CH2:11][CH2:10][CH2:9]2)[NH:4][C:5](=[O:20])[C:6]1=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 123371,4-DiiodobutaneHCID 516892Sodium BicarbonateHCID 68777664(4aRS,5SR,8aRS)-5-amino-1-benzylperhydroquinoxaline-2,3-dione

Product 1

HCID 68777117(4aRS,5SR,8aRS)-1-benzyl-5-(pyrrolidin-1-yl)perhydroquinoxaline-2,3-dione

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(4aRS,5SR,8aRS)-5-Amino-1-benzylperhydroquinoxaline-2,3-dione (3.06 g, 11.2 mmol) was dissolved in CH3CN (300 ml). NaHCO3 (6.4 g, 76.2 mmol) and 1,4-diiodobutane (13.9 g, 44.8 mmol, 5.9 ml) were added and the mixture was heated under reflux for 18 hours. NaHCO3 was separated off with a blue-band filter (Schleicher&Schuell) and the yellow solution was concentrated in vacuo. The solid was taken up in CH2Cl2 and the mixture was extracted by shaking three times with HCl (1 N). The aqueous phase was then brought to pH 8 with NaOH (2 N) and extracted by shaking three times with CH2Cl2. The organic phases were dried over Na2SO4 and evaporated in vacuo. A pale yellow solid was obtained.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. customNaHCO3 was separated off with a blue-band filter (Schleicher&Schuell)
  4. concentrationthe yellow solution was concentrated in vacuo
  5. extractionthe mixture was extracted
  6. extractionextracted
  7. stirringby shaking three times with CH2Cl2
  8. dry with materialThe organic phases were dried over Na2SO4
  9. customevaporated in vacuo
  10. customA pale yellow solid was obtained

Sources & evidence

ORD record
ord-f8523a2b440a489c84e2be6a3be9cf77
Source dataset
uspto-grants-2012_11
Patent number
US08309725B2

Linked notes

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