Phthalic Anhydride → 2-[(2R)-1-hydroxypropan-2-yl]-2,3-dihydro-1H-isoindole-1,3-dione

HRID 872465Notes

Reaction equation

HRID 872465 reaction equation
[NH2:1][C@@H:2]([CH2:4][OH:5])[CH3:3].[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(Cl)Cl>[OH:5][CH2:4][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])[CH3:3]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 80308(R)-(-)-2-Amino-1-propanol

Product 1

HCID 6418462-[(2R)-1-hydroxypropan-2-yl]-2,3-dihydro-1H-isoindole-1,3-dioneYield 85.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

D-Alaninol (3.90 ml, 50 mmol) and phthalic anhydride (7.41 g, 50 mmol) were heated at 160° C. for 30 min. To cooled reaction mixture was added ice water and DCM. Organic phase was collected and the water phase was extracted with DCM. Combined organic phases were dried over Na2SO4 and evaporated to obtain 8.75 g (85%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 1.32 (d, 3H), 3.54 (m, 1H), 3.84 (m, 1H), 4.26 (m, 1H), 4.91 (m, 1H), 7.84 (m, 4H).

Workup

  1. temperatureTo cooled
  2. customreaction mixture
  3. customOrganic phase was collected
  4. extractionthe water phase was extracted with DCM
  5. dry with materialCombined organic phases were dried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-12c90facedb94017adddbf5173236d38
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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