phenyl N-benzyloxycarbamate → 1-(N-benzyloxycarbamoyl)-3-(3,5-di-tert-butyl-4-hydroxybenzylidene)pyrrolidin-2-one

HRID 1109292Notes

Reaction equation

HRID 1109292 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:15]=[C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:17]=1[OH:18])[CH:8]=[C:9]1[CH2:13][CH2:12][NH:11][C:10]1=[O:14])([CH3:4])([CH3:3])[CH3:2].[CH2:23]([O:30][NH:31][C:32](=O)[O:33]C1C=CC=CC=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>N1C=CC=CC=1>[CH2:23]([O:30][NH:31][C:32]([N:11]1[CH2:12][CH2:13][C:9](=[CH:8][C:7]2[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:17]([OH:18])=[C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:15]=2)[C:10]1=[O:14])=[O:33])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 11644415phenyl N-benzyloxycarbamateHCID 538962973-(3,5-Di-tert-butyl-4-hydroxybenzylidene)-2-pyrrolidone

Product 1

HCID 538058911-(N-benzyloxycarbamoyl)-3-(3,5-di-tert-butyl-4-hydroxybenzylidene)pyrrolidin-2-oneYield 61%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-(3,5-Di-tert-butyl-4-hydroxybenzylidene)pyrrolidin-2-one (600 mg, 2 mmole) and phenyl N-benzyloxycarbamate (490 mg, 2.01 mmole) were dissolved into 8 ml of pyridine and the solution was heated under reflux for 12 hours. The reaction mixture was evaporated and the obtained residue was dissolved into ethyl acetate, which was washed with an aqueous solution of 0.1N hydrochloric acid, water, and saturated brine, dried over magnesium sulfate, and evaporated. The obtained residue was separated by using silica gel chromatography (toluene:ethyl acetate=10:1) and recrystallized from dichloromethane/n-hexane, whereby 550 mg of the objective compound (Ia-10) was obtained in 61% yield.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 12 hours
  3. customThe reaction mixture was evaporated
  4. dissolutionthe obtained residue was dissolved into ethyl acetate, which
  5. washwas washed with an aqueous solution of 0.1N hydrochloric acid, water, and saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe obtained residue was separated
  9. customrecrystallized from dichloromethane/n-hexane

Sources & evidence

ORD record
ord-e0e1b7afab6d407aab8c805ffb493e9d
Source dataset
uspto-grants-1994_06
Patent number
US05319100

Reaction notes

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