Sodium Hydroxide → HCID 58289816, compound

HRID 2088747Notes

Reaction equation

HRID 2088747 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[C:13](=O)[N:12]([CH3:18])[C:11]2([CH3:20])[CH3:19].[OH-].[Na+]>C1COCC1>[NH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[CH2:13][N:12]([CH3:18])[C:11]2([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 58289863HCID 58289863, compound

Product 1

HCID 58289816HCID 58289816, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

29 mg of lithiumaluminium hydride was added to 3.8 mL of a THF solution of 89 mg of 5-amino-2,3,3,-trimethylisoindolin-1-one, and the mixture was stirred at 70° C. for 3 hours. 0.05 mL of aqueous 5 M sodium hydroxide solution was added to it, and the solvent was evaporated away under reduced pressure. 10% methanol/chloroform was added to the residue, the mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified through basic silica gel column chromatography (hexane/ethyl acetate) to obtain 45 mg of the entitled compound as a pale yellow solid.

Workup

  1. customthe solvent was evaporated away under reduced pressure
  2. addition10% methanol/chloroform was added to the residue
  3. filtrationthe mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified through basic silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-dac2e850d5074a03ba041aba2f64800d
Source dataset
uspto-grants-2013_05
Patent number
US08436004B2

Reaction notes

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