Bromocyclopentane → 2-(cyclopentyloxy)-1H-isoindole-1,3(2H)-dione

HRID 29151

Reaction equation

HRID 29151 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].[CH:13]1(Br)[CH2:17][CH2:16][CH2:15][CH2:14]1.N12CCCN=C1CCCCC2>CN(C)C=O>[CH:13]1([O:1][N:2]2[C:3](=[O:12])[C:4]3[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]2=[O:7])[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 8728BromocyclopentaneHCID 10665N-HydroxyphthalimideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 102632872-(cyclopentyloxy)-1H-isoindole-1,3(2H)-dioneYield 80.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of N-hydroxypthalimide (10.00 g, 61.3 mmol), cyclopentylbromide (8.21 mL, 76.63 mmol), and 1,8-diazabicyclo[5.4.0]undec-7-ene (13.75 mL, 76.6 mmol) were combined under an Argon atmosphere in dimethylformamide (50 mL). The mixture was heated to 55° C. and stirred vigorously for 1.5 hours. After cooling to ambient temperature, the solvent was removed in vacuo and the residue was partitioned between ethyl acetate and 1N hydrochloric acid. After separating the phases, the aqueous layer was extracted again with ethyl acetate. The combined organic layers were washed with 5% w/v potassium carbonate, saturated aqueous brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The residue was triturated with hexane, filtered, and dried under high vacuum to provide 2-(cyclopentyloxy)-1H-isoindole-1,3(2H)-dione (11.37 g, 80%). H1-NMR (chloroform-D3): 1.61 (m, 2H), 1.77 (m, 2H), 1.97 (m, 4H), 4.91 (m, 1H), 7.73 (m, 2H), 7.82 (m, 2H). MS(ESI): 254 (M+Na).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. customthe solvent was removed in vacuo
  3. customthe residue was partitioned between ethyl acetate and 1N hydrochloric acid
  4. customAfter separating the phases
  5. extractionthe aqueous layer was extracted again with ethyl acetate
  6. washThe combined organic layers were washed with 5% w/v potassium carbonate, saturated aqueous brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe residue was triturated with hexane
  11. filtrationfiltered
  12. customdried under high vacuum

Sources & evidence

ORD record
ord-7e206d4751dd4d13b855a736a52aa5b3
Source dataset
uspto-grants-2008_09
Patent number
US07419967B2

Linked notes

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