Reacción #1483056

Ecuación de reacción

(E)-cyclooct-4-enol

triethylamine

N,N-disuccinimidyl carbonate

→

title compound

Rendimiento 75.5%

(E)-cyclooct-4-enyl 2,5-dioxopyrrolidin-1-yl carbonate

Rendimiento 75.5%

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Otro(approximately 48 hours)
2. 2
   OtroThe acetonitrile was removed by rotary evaporation
3. 3
   Lavadowashed with 0.1M HCl
4. 4
   Secadodried with magnesium sulfate
5. 5
   OtroThe ether was evaporated
6. 6
   Otrothe resulting oil was purified by column chromatography (1:1 Ethyl Acetate:Hexane)

Procedimiento

50 mg of (E)-cyclooct-4-enol (major isomer) and 0.2 mL triethylamine were added to 3 mL anhydrous acetonitrile. To this solution was slowly added 250 mg of N,N-disuccinimidyl carbonate. The reaction mixture was stirred at room temperature until thin layer chromatography revealed that the reaction was complete (approximately 48 hours). The acetonitrile was removed by rotary evaporation and the remaining residue was suspended in ether, washed with 0.1M HCl followed by brine, and dried with magnesium sulfate. The ether was evaporated and the resulting oil was purified by column chromatography (1:1 Ethyl Acetate:Hexane) yielding 80 mg (75% yield) of the title compound. 1H NMR (400 MHz CDCl3): δ 5.65-5.54 (m, 1H), 5.5-5.4 (m, 1H), 4.5-4.4 (m, 1H), 2.88-2.78 (s, 4H), 2.45-2.3 (m, 2H), 2.2-1.5 (m, 8H).

Fuente