Phthalimide → HCID 86705497, compound

HRID 2279502Notes

Reaction equation

HRID 2279502 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9](O)[CH2:10][O:11][CH3:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:14]1(=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16](=[O:23])[NH:15]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([N:15]2[C:16](=[O:23])[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:14]2=[O:24])[CH2:10][O:11][CH3:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 86705498HCID 86705498, compound

Product 1

HCID 86705497HCID 86705497, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 194 (1.25 g, 5.65 mmol) and THF (10 mL) at RT was added sequentially isoindoline-1,3-dione (0.915 g, 6.22 mmol) and PPh3 (2.22 g, 8.48 mmol) followed by the dropwise addition of DEAD (3.34 mL, 8.48 mmol). The reaction was warmed to RT, stirred for 20 h and then concentrated to dryness. Ether (300 mL) was added, and the resulting solid was filtered and discarded. The filtrate was then poured into water, and extracted with DCM. The combined organic fractions were dried (MgSO4), filtered and concentrated. The crude product was purified by SiO2 chromatography eluting with DCM to afford 1.9 g (96.0%) of (S)-2-(1-(3,4-dichlorophenyl)-2-methoxyethyl)isoindoline-1,3-dione (196).

Workup

  1. concentrationconcentrated to dryness
  2. additionEther (300 mL) was added
  3. filtrationthe resulting solid was filtered
  4. additionThe filtrate was then poured into water
  5. extractionextracted with DCM
  6. dry with materialThe combined organic fractions were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by SiO2 chromatography
  10. washeluting with DCM

Sources & evidence

ORD record
ord-cbbc7884febe4b8391ec68f7db83c1e5
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

Loading…