Water → (R)-2-(1-hydroxy-4-methylpentan-2-yl)isoindoline-1,3-dione

HRID 1453423Notes

Reaction equation

HRID 1453423 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[NH2:12][C@@H:13]([CH2:18][OH:19])[CH2:14][CH:15]([CH3:17])[CH3:16].O>C1COCC1>[OH:19][CH2:18][C@H:13]([N:12]1[C:1](=[O:11])[C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]1=[O:6])[CH2:14][CH:15]([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 6811Phthalic AnhydrideHCID 2724002D(-)-Leucinol

Product 1

HCID 66772663(R)-2-(1-hydroxy-4-methylpentan-2-yl)isoindoline-1,3-dioneYield 47.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

Phthalic anhydride (10.30 g, 69.55 mmol) and D-Leucinol (8.15 g, 69.55 mmol) were mixed in THF (100 mL), the reaction mixture was heated at 85° C. and refluxed for 18 hours. After cooling to room temperature, water was added and the solution was extracted with EtOAC, the extracts were washed with 1 N HCl, water, aq. NaHCO3, water and brine, dried over MgSO4, filtered and evaporated to give 8.1 g of (R)-2-(1-hydroxy-4-methylpentan-2-yl)isoindoline-1,3-dione (47%). 1H NMR (500 MHz, CDCl3): δ 0.94 (m, 6H); 1.54 (m, 2H); 1.99 (m, 1H); 3.86 (m, 1H); 4.04 (m, 1H); 4.47 (m, 1H); 7.72 (m, 2H); 7.83 (m, 2H).

Workup

  1. temperaturerefluxed for 18 hours
  2. temperatureAfter cooling to room temperature
  3. extractionthe solution was extracted with EtOAC
  4. washthe extracts were washed with 1 N HCl, water, aq. NaHCO3, water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-8e327361ddd14a41be329f5ad4a3faea
Source dataset
uspto-grants-2009_01
Patent number
US07476399B2

Reaction notes

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