Phthalic Anhydride → 2-[(1S)-2-Hydroxy-1-methylethyl]-1H-isoindole-1,3(2H)-dione

HRID 2065787Notes

Reaction equation

HRID 2065787 reaction equation
[NH2:1][C@@H:2]([CH3:5])[CH2:3][OH:4].[C:6]1(=O)[O:11][C:9](=[O:10])[C:8]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:7]12>C(OCC)(=O)C>[OH:4][CH2:3][C@@H:2]([N:1]1[C:9](=[O:10])[C:8]2[C:7](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:6]1=[O:11])[CH3:5]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 80307L-Alaninol

Product 1

HCID 124997532-[(1S)-2-Hydroxy-1-methylethyl]-1H-isoindole-1,3(2H)-dioneYield 99.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of (2S)-2-aminopropan-1-ol (26 mL, 333 mmol) and phthalic anhydride (51.7 g, 349.4 mmol) is heated at 140° C. overnight. During this time the solid becomes an orange liquid. The reaction is cooled to RT and diluted with ethyl acetate (10 mL/g). The organic phase is washed with saturated NaHCO3 and 10% citric acid, dried over MgSO4, filtered, and concentrated to afford the title compound (68.3 g, 98%) as a white solid that is used without further purification. LC-ES/MS m/z 206 (M+1).

Workup

  1. temperatureThe reaction is cooled to RT
  2. washThe organic phase is washed with saturated NaHCO3 and 10% citric acid
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c65a6fd8e5e74dd8b115b21d7ae400bb
Source dataset
uspto-grants-2012_10
Patent number
US08288548B2

Reaction notes

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