Phthalimide → (S)-2-(2-(4-Fluorophenyl)propyl)isoindoline-1,3-dione

HRID 2359905Notes

Reaction equation

HRID 2359905 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH3:11])[CH2:9]O)=[CH:4][CH:3]=1.[C:12]1(=[O:22])[NH:16][C:15](=[O:17])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH3:11])[CH2:9][N:16]2[C:12](=[O:22])[C:13]3[C:14](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:15]2=[O:17])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 12969931(S)-2-(4-Fluorophenyl)propan-1-ol

Product 1

HCID 67453498(S)-2-(2-(4-Fluorophenyl)propyl)isoindoline-1,3-dioneYield 59.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-2-(4-fluorophenyl)propan-1-ol (824 mg, 5.35 mmol, 1.0 equiv), phthalimide (0.824 g, 5.6 mmol, 1.05 equiv), and triphenyl phosphine (2.11 g, 8.03 mmol, 1.5 equiv) in dry THF (18 mL) was added dropwise diethyl azadicarboxylate (DEAD) (3.65 mL, 15% in toluene, 8.03 mmol, 1.5 equiv). The reaction mixture was stirred over 72 h and then concentrated in vacuo. Purification by silica gel chromatography (15-25% EtOAc/Hexanes) provided the title compound (0.9 g, 59%) which was characterized by 1H NMR.

Workup

  1. concentrationconcentrated in vacuo
  2. customPurification by silica gel chromatography (15-25% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-681e2bda308346c5813beef1b4fe133d
Source dataset
uspto-grants-2014_04
Patent number
US08686007B2

Reaction notes

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