Reacción #2358491

Ecuación de reacción

water

tert-butyl 2-oxo-3,3a,4,6a-tetrahydrocyclopenta[b]pyrrole-1-carboxylate

tert-butoxybis(dimethylamino)methane

→

desired compound

Rendimiento 58.0%

tert-butyl-3-(dimethylaminomethylene)-2-oxo-4,6a-dihydro-3aH-cyclopenta[b]pyrrole-1-carboxylate

Rendimiento 58.0%

Disolventes

ethyl acetate

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaIt was then cooled to room temperature
2. 2
   Extracciónextracted 3 times
3. 3
   LavadoThe combined organic layers were washed with brine
4. 4
   Otrodried
5. 5
   Concentraciónconcentrated
6. 6
   Otropurified by flash chromatography (5% MeOH in CH2Cl2)

Procedimiento

To a solution of tert-butyl 2-oxo-3,3a,4,6a-tetrahydrocyclopenta[b]pyrrole-1-carboxylate IV-1 (500 mg, 2.23 mmol) in toluene (11 mL) was added tert-butoxybis(dimethylamino)methane (1.39 mL, 6.71 mmol) The solution was heated for 2 h at 110° C. It was then cooled to room temperature, poured into water (20 mL), diluted with ethyl acetate (20 mL), and extracted 3 times. The combined organic layers were washed with brine, dried, concentrated and purified by flash chromatography (5% MeOH in CH2Cl2) giving the desired compound as a brown solid (367 mg, 58%); 1H NMR (400 MHz, CDCl3) 7.12 (1H, s), 5.99 (1H, m), 5.85 (1H, m), 4.91 (1H, d), 3.70 (1H, m), 3.03 (6H, s), 2.79 (1H, m), 2.40 (1H, dd), 1.54 (9H, s); LCMS (Method A): 0.83 min; ES+279 (M+H+).

Fuente