HCID 21994134, compound → tert-Butyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethylidene)piperidine-1-carboxylate

HRID 1978308Notes

Reaction equation

HRID 1978308 reaction equation
Br[CH2:2][CH:3]=[C:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.[C:17]1(=[O:27])[NH:21][C:20](=[O:22])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12.[K]>CN(C)C=O.O>[C:13]([O:12][C:10]([N:7]1[CH2:8][CH2:9][C:4](=[CH:3][CH2:2][N:21]2[C:20](=[O:22])[C:19]3=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]3[C:17]2=[O:27])[CH2:5][CH2:6]1)=[O:11])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 2

HCID 21994134HCID 21994134, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 21993713tert-Butyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethylidene)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 5.775 g (19.900 mM) of tert-butyl 4-(2-bromoethylidene)piperidine-1-carboxylate and 4.05 g (21.9 mM) of potassium phthalimide in 100 ml of N,N-dimethylformamide was stirred at 100° C. for 1 hour. This reaction mixture was poured in water and extracted with 3 portions of ethyl acetate. The pooled organic layer was dried over anhydrous magnesium sulfate (MgSO4) and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=6/1 to 3/1) to provide the title compound.

Workup

  1. extractionextracted with 3 portions of ethyl acetate
  2. dry with materialThe pooled organic layer was dried over anhydrous magnesium sulfate (MgSO4)
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=6/1 to 3/1)

Sources & evidence

ORD record
ord-978f7f91bbf84dbeb46ae15af637ecff
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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