Water → HCID 33699142, compound

HRID 2357429Notes

Reaction equation

HRID 2357429 reaction equation
O.[Al].[Li].[NH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](C2CC(=O)NC2=O)=[CH:5]1.[OH-].[Na+].O>C1COCC1>[N:4]1([C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[NH:4][CH:5]=2)[CH2:12][CH2:7][CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 3633263-(1H-indol-3-yl)pyrrolidine-2,5-dioneHCID 57438284HCID 57438284, compound

Product 1

HCID 33699142HCID 33699142, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Lithium aluminum hydrate (2.86 g, 75.6 mmole) was suspended in dry THF (50 ml) with the exclusion of atmospheric moisture. The suspension was cooled by means of an ice-salt bath to an internal temperature of ca. 0° C. 3-(1H-indol-3-yl)-pyrrolidine-2,5-dione (3.24 g, 15.12 mmole) was then added in portions within 15 minutes. After ca. 1 hour the reaction mixture had reached RT and was then boiled under reflux for 32 hours. After the reaction mixture had cooled moist THF (5 ml water in 25 ml THF) was first carefully added, followed by 5M sodium hydroxide (3 ml) and finally water (3 ml). The reaction mixture was stirred for 20 minutes and filtered through diatomaceous earth. The solvent mixture obtained after washing the filter cake several times with methanol was evaporated to dryness. The oily residue obtained was purified by column chromatography on silica gel with methanol/30% aqueous ammonia (20:1). The product was filtered again through diatomaceous earth. The solution obtained by washing the diatomaceous earth several times with chloroform was evaporated to dryness. The desired product was thereby obtained as a viscous oil in a yield of 670 mg (24%).

Workup

  1. temperatureunder reflux for 32 hours
  2. additionwas first carefully added
  3. filtrationfiltered through diatomaceous earth
  4. customThe solvent mixture obtained
  5. washafter washing the filter cake several times with methanol
  6. customwas evaporated to dryness
  7. customThe oily residue obtained
  8. customwas purified by column chromatography on silica gel with methanol/30% aqueous ammonia (20:1)
  9. filtrationThe product was filtered again through diatomaceous earth
  10. customThe solution obtained
  11. washby washing the diatomaceous earth several times with chloroform
  12. customwas evaporated to dryness

Sources & evidence

ORD record
ord-5c7f5f5fb4b14785b5adf05c276c104f
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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