HCID 54543898, compound → HCID 19041655, compound

HRID 1683994Notes

Reaction equation

HRID 1683994 reaction equation
[Br:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH:18]([CH3:25])[CH:19]=[CH:20][C:21]([O:23][CH3:24])=[O:22])=[C:8]2[CH3:26])=[CH:4][CH:3]=1>C1COCC1.CO.BrCCBr>[Br:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH:18]([CH3:25])[CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[C:8]2[CH3:26])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 54543898HCID 54543898, compound

Product 1

HCID 19041655HCID 19041655, compoundYield 32.7%

Reagents, catalysts & solvents 2

HCID 78391,2-DibromoethaneCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To the ester (520 mg, 1.17 mmol) of Step 3 dissolved in a THF/MeOH mixture (4.0 mL/20.0 mL) was added an excess of Mg and a few drops of 1,2-dibromoethane. The reduction was initated by heating at reflux. After standing for a few hours at room temperature, the reaction mixture was quenched by the addition of a 25% aqueous NH4OAc solution, extracted with EtOAc, dried over MgSO4 and evaporated in vacuo. The desired reduced product was purified by flash chromatography (25% EtOAc in hexane) to provide 170 mg of an oil.

Workup

  1. temperatureby heating
  2. temperatureat reflux
  3. waitAfter standing for a few hours at room temperature
  4. customthe reaction mixture was quenched by the addition of a 25% aqueous NH4OAc solution
  5. extractionextracted with EtOAc
  6. dry with materialdried over MgSO4
  7. customevaporated in vacuo
  8. customwas purified by flash chromatography (25% EtOAc in hexane)

Sources & evidence

ORD record
ord-e3eab64e0da8479bb4efc38b069ab0e3
Source dataset
uspto-grants-1997_06
Patent number
US05639780

Reaction notes

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