Реакция #2358491

Уравнение реакции

water

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

tert-butoxybis(dimethylamino)methane

→

desired compound

Выход 58.0%

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

Выход 58.0%

Растворители

ethyl acetate

toluene

Условия реакции

Обработка

1. 1
   ТемператураIt was then cooled to room temperature
2. 2
   Экстракцияextracted 3 times
3. 3
   ПромывкаThe combined organic layers were washed with brine
4. 4
   Другоеdried
5. 5
   Концентрированиеconcentrated
6. 6
   Другоеpurified by flash chromatography (5% MeOH in CH2Cl2)

Методика

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+).

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