Phthalimide → 2-(5-Phenylpentyl)isoindoline-1,3-dione

HRID 1486557Notes

Reaction equation

HRID 1486557 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:32]1(=[O:42])[NH:36][C:35](=[O:37])[C:34]2=[CH:38][CH:39]=[CH:40][CH:41]=[C:33]12.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:36]2[C:32](=[O:42])[C:33]3[C:34](=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:35]2=[O:37])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 615235-Phenyl-1-pentanolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 6261932-(5-Phenylpentyl)isoindoline-1,3-dioneYield 77.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

5-Phenylpentan-1-ol (0.50 g, 3 mmol), triphenylphosphine (0.45 g, 3 mmol), and phthalimide (0.80 g, 3 mmol) were vigorously stirred in dry THE (5 mL) while cooling to 0° C. A solution of DEAD (0.62 g, 3 mmol) in 5 mL of dry THF was added dropwise to the cooled mixture. After stirring at room temperature for 12 his, the solvent was removed by reduced pressure. The crude was purified by column chromatography using a Teledyne ISCO apparatus (cyclohexane:EtOAc 90:10) to afford the title compound (0.68 g, 76%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 1.22-1.34 (m, 2H), 1.49-1.69 (m, 4H), 2.52-2.58 (m, 2H), 3.56 (t, J=7.06 Hz, 2H), 7.06-7.27 (m, 5H), 7.75-7.95 (m, 4H). MS (ESI) m/z: 334 [M-H]−.

Workup

  1. customin dry THE (5 mL)
  2. customthe solvent was removed by reduced pressure
  3. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-37af43d8f7774fdd8ee7b3d2893a7988
Source dataset
uspto-grants-2016_08
Patent number
US09428465B2

Reaction notes

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