Phthalimide → HCID 86705491, compound

HRID 2279486Notes

Reaction equation

HRID 2279486 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9](O)[CH2:10][CH3:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:13]1(=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:22])[NH:14]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[OH-].[Na+]>C(Cl)Cl.C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([N:14]2[C:15](=[O:22])[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:13]2=[O:23])[CH2:10][CH3:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

8

Reactant 5

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 5363146Diisopropyl azodicarboxylateHCID 25665794(αS)-3,4-Dichloro-α-ethylbenzenemethanol

Product 1

HCID 86705491HCID 86705491, compoundYield 37.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 158 (3.45 g, 16.5 mmol) and THF (45 mL) cooled to 0° C. was added isoindoline-1,3-dione (2.67 g, 18.1 mmol) and PPh3 (6.49 g, 24.7 mmol) followed by the dropwise addition of neat DIAD (6.67 g, 33.0 mmol). The reaction was warmed to RT and stirred 18 h. The reaction was stirred with NaOH 2N (50 mL) and DCM (50 mL) for 2 h (emulsion) and then extracted with DCM. The combined organic fractions were dried (Na2SO4), filtered, and concentrated. The residue was triturated with hexane/EtOAc (1:1) and the precipitated POPh3 was filtered. The filtrate was concentrated and chromatographed (Isolera) eluting with hexane/EtOAc (9:1) to afford 2.05 g (32%) of (R)-2-(1-(3,4-dichlorophenyl)propyl)isoindoline-1,3-dione (160)

Workup

  1. extractionextracted with DCM
  2. dry with materialThe combined organic fractions were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was triturated with hexane/EtOAc (1:1)
  6. filtrationthe precipitated POPh3 was filtered
  7. concentrationThe filtrate was concentrated
  8. customchromatographed (Isolera)
  9. washeluting with hexane/EtOAc (9:1)

Sources & evidence

ORD record
ord-e3b72f0b8e294661a685368e707df26b
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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