N-Carbethoxyphthalimide → 2-[2-(5-Ethyl-2-methoxy-6-methyl-3-pyridyl)-2-hydroxy-ethyl]isoindoline-1,3-dione

HRID 1033018Notes

Reaction equation

HRID 1033018 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH:9]([OH:12])[CH2:10][NH2:11])=[CH:7][C:6]([CH2:13][CH3:14])=[C:5]([CH3:15])[N:4]=1.C(N1[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]2[C:22]1=[O:31])(OCC)=O>C(O)C>[CH3:1][O:2][C:3]1[C:8]([CH:9]([OH:12])[CH2:10][N:11]2[C:25](=[O:26])[C:24]3=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]3[C:22]2=[O:31])=[CH:7][C:6]([CH2:13][CH3:14])=[C:5]([CH3:15])[N:4]=1

Participants

4

Reactant 2

HCID 31187N-CarbethoxyphthalimideHCID 103307592-Amino-1-(5-ethyl-2-methoxy-6-methylpyridin-3-yl)ethan-1-ol

Product 1

HCID 4642772-[2-(5-Ethyl-2-methoxy-6-methyl-3-pyridyl)-2-hydroxy-ethyl]isoindoline-1,3-dioneYield 15%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2-methoxy-3-(2-amino-1-(R/S)hydroxyethyl)-5-ethyl-6-methylpyridine (345 mg, 1.64 mmol) in ethanol (5 mL) was added N-(carbethoxy)-phthalimide (373 mg, 1.70 mmol). The reaction was stirred for six hours as suspension dissolved. The solvent was evaporated and the viscous residue triturated with ethyl acetate/diethyl ether as product crystallized. By filtration 273 mg (49%) of pure product was collected, m.p. 134°-135° C. These mother liquors were flash chromatographed on silica gel and eluted with 20% ethyl acetate/80% hexane to give an additional 83 mg (15%) of product.

Workup

  1. dissolutiondissolved
  2. customThe solvent was evaporated
  3. customthe viscous residue triturated with ethyl acetate/diethyl ether as product
  4. customcrystallized
  5. filtrationBy filtration 273 mg (49%) of pure product
  6. customwas collected
  7. customchromatographed on silica gel
  8. washeluted with 20% ethyl acetate/80% hexane

Sources & evidence

ORD record
ord-5387b2b98d364c26994a303aaab65ea6
Source dataset
uspto-grants-1994_05
Patent number
US05308854

Reaction notes

Loading…