Potassium Carbonate → HCID 23361318, compound

HRID 233046Notes

Reaction equation

HRID 233046 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:12][CH2:11][CH2:10][N:9]2[CH2:13][CH2:14][N:15]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]2=[O:25])[CH:5]=[CH:6][CH:7]=1.[CH3:26][N:27]=[C:28]=[O:29].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH3:26][NH:27][C:28](=[O:29])[O:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]2[CH2:12][CH2:11][CH2:10][N:9]2[CH2:13][CH2:14][N:15]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]2=[O:25])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12228Methyl IsocyanateHCID 15291375HCID 15291375, compound

Product 1

HCID 23361318HCID 23361318, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{2-[2-(3-hydroxyphenyl)-1-pyrrolidinyl]ethyl}-1H-isoindole-1,3(2H)dione (0.71) in dry tetrahydrofuran (35 ml) was added methyl isocyanate (0.13 ml) followed by milled potassium carbonate (0.38 g) at ambient temperature, under nitrogen. The reaction mixture was stirred for 45 mins, filtered through a pad of celite, and the filter cake was washed with ethyl acetate. The combined filtrates were concentrated, and the residue was triturated with petroleum ether. The residue was purified by flash column chromatography (silica gel, 1:1 ethyl acetate/heptane). The appropriate fractions were collected and concentrated to afford 0.78 g (94%) of product. Recrystallization from dichloromethane/petroleum ether gave the analytical sample, mp 96°-98° C.

Workup

  1. filtrationfiltered through a pad of celite
  2. washthe filter cake was washed with ethyl acetate
  3. concentrationThe combined filtrates were concentrated
  4. customthe residue was triturated with petroleum ether
  5. customThe residue was purified by flash column chromatography (silica gel, 1:1 ethyl acetate/heptane)
  6. customThe appropriate fractions were collected
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2617167abd5d42b8aa17327e99f44e6d
Source dataset
uspto-grants-1997_01
Patent number
US05591856

Reaction notes

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