N-bromobutanimide → HCID 14428789, compound

HRID 330484Notes

Reaction equation

HRID 330484 reaction equation
[C:1]([O:4][C@@H:5]1[C@@:34]2([CH3:35])[C:9](=[CH:10][CH2:11][C@@H:12]3[C@@H:33]2[CH2:32][CH2:31][C@@:30]2([CH3:36])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C@H:17]([CH3:29])[C@H:18]([O:25][C:26](=[O:28])[CH3:27])[CH2:19][CH2:20][C:21]([OH:24])([CH3:23])[CH3:22])[CH2:8][C@@H:7]([O:37][C:38](=[O:40])[CH3:39])[CH2:6]1)(=[O:3])[CH3:2].BrN1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[C:1]([O:4][C@@H:5]1[C@@:34]2([CH3:35])[C:9](=[CH:10][CH:11]=[C:12]3[C@@H:33]2[CH2:32][CH2:31][C@@:30]2([CH3:36])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C@H:17]([CH3:29])[C@H:18]([O:25][C:26](=[O:28])[CH3:27])[CH2:19][CH2:20][C:21]([OH:24])([CH3:22])[CH3:23])[CH2:8][C@@H:7]([O:37][C:38](=[O:40])[CH3:39])[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 14428785HCID 14428785, compound

Product 1

HCID 14428789HCID 14428789, compoundYield 9.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

18.4 mg of (22R)-1α,3β,22-triacetoxycholest-5-en-25-ol (IVa1) was dissolved in 2 ml of carbon tetrachloride; the solution was refluxed under heating under argon gas atmosphere, and then 8.2 mg of N-bromo-succinimide was added to the mixture. After refluxing for 25 minutes, the mixture was cooled with ice-water, and the insoluble material was removed by filtration. The filtrate was concentrated under reduced pressure, and the residue was dissolved in 1.5 ml of xylene, and the solution was added dropwise to a refluxed solution of 1 ml of xylene and 1.5 ml of 2,4,6-collidine under argon gas stream atmosphere. After the dropping was completed, the mixture was refluxed for 10 minutes. The mixture was diluted with ethyl acetate, and the mixture was washed with 2N-hydrochloric acid, saturated aqueous sodium hydrogen carbonate, and water, successively, and dried over magnesium sulfate. The residue was dissolved in 10 ml of acetone, and after adding thereto 5 mg of p-toluenesulfonic acid, the mixture was stirred overnight under argon gas stream atmosphere under dark condition at room temperature. The reaction solution was diluted with ethyl acetate, washed with water, and dried over magnesium sulfate. The solvent was removed by distillation, and the residue was subjected to preparative thin layer chromatography (solvent: n-hexane-ethyl acetate=2:1; developing: 5 times) for purification to give 1.75 mg of (22R)-1α,3β,22-triacetoxycholest-5,7-dien-25-ol (Va1).

Workup

  1. temperaturethe solution was refluxed
  2. temperatureunder heating under argon gas atmosphere
  3. temperatureAfter refluxing for 25 minutes
  4. customthe insoluble material was removed by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. dissolutionthe residue was dissolved in 1.5 ml of xylene
  7. additionthe solution was added dropwise to a refluxed solution of 1 ml of xylene and 1.5 ml of 2,4,6-collidine under argon gas stream atmosphere
  8. temperaturethe mixture was refluxed for 10 minutes
  9. additionThe mixture was diluted with ethyl acetate
  10. washthe mixture was washed with 2N-hydrochloric acid, saturated aqueous sodium hydrogen carbonate, and water
  11. dry with materialsuccessively, and dried over magnesium sulfate
  12. dissolutionThe residue was dissolved in 10 ml of acetone
  13. additionafter adding
  14. additionThe reaction solution was diluted with ethyl acetate
  15. washwashed with water
  16. dry with materialdried over magnesium sulfate
  17. customThe solvent was removed by distillation
  18. customthe residue was subjected to preparative thin layer chromatography (solvent: n-hexane-ethyl acetate=2:1; developing: 5 times) for purification

Sources & evidence

ORD record
ord-983fb6ec5bd54cfc92c389be72f59c79
Source dataset
uspto-grants-1990_01
Patent number
US04897387

Reaction notes

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