反応 #2358491

反応方程式

water

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

tert-butoxybis(dimethylamino)methane

→

desired compound

収率 58.0%

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

収率 58.0%

溶媒

ethyl acetate

toluene

反応条件

後処理

1. 1
   温度It was then cooled to room temperature
2. 2
   抽出extracted 3 times
3. 3
   洗浄The combined organic layers were washed with brine
4. 4
   その他dried
5. 5
   濃縮concentrated
6. 6
   その他purified by flash chromatography (5% MeOH in CH2Cl2)

実験手順

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+).

出典