Reacción #57429

Ecuación de reacción

N-hydroxypthalimide

cyclopentylbromide

1,8-diazabicyclo[5.4.0]undec-7-ene

→

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

Rendimiento 80.2%

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling to ambient temperature
2. 2
   Otrothe solvent was removed in vacuo
3. 3
   Otrothe residue was partitioned between ethyl acetate and 1N hydrochloric acid
4. 4
   OtroAfter separating the phases
5. 5
   Extracciónthe aqueous layer was extracted again with ethyl acetate
6. 6
   LavadoThe combined organic layers were washed with 5% w/v potassium carbonate, saturated aqueous brine
7. 7
   Secadodried over anhydrous magnesium sulfate
8. 8
   Filtraciónfiltered
9. 9
   Otroevaporated in vacuo
10. 10
    OtroThe residue was triturated with hexane
11. 11
    Filtraciónfiltered
12. 12
    Otrodried under high vacuum

Procedimiento

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).

Fuente