Reaktion #1345315

Reaktionsgleichung

Cesium carbonate

aziridine

2-(2-Benzo[1,3]dioxol-5-yl-aziridin-1-yl)-but-2-enedioic acid dimethyl ester

→

27

Ausbeute 92.5%

4-Benzo[1,3]dioxol-5-yl-1H-pyrrole-2,3-dicarboxylic acid dimethyl ester

Ausbeute 92.5%

Lösungsmittel

1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction vessel was sealed under argon
2. 2
   TemperaturThe reaction mixture was cooled to 25° C.
3. 3
   Filtrationgravity filtered
4. 4
   Einengenconcentrated by rotary evaporation

Vorschrift

Cesium carbonate (110 mg, 0.30 mmol, 4.0 equiv) was added to a stirred solution of aziridine 26 (25 mg, 82 μmol, 1.0 equiv) in 1,4-dioxane (12 mL) at 25° C. The reaction vessel was sealed under argon and heated to 100° C. via oil bath for 20 h. The reaction mixture was cooled to 25° C., gravity filtered, and concentrated by rotary evaporation to afford 27 (23 mg, 92% yield) as a dark orange film. 1H NMR (500 MHz, CDCl3) δ 10.22 (br d, 1H, J=11 Hz, NH), 7.43 (dd, 1H, J=14, 11 Hz, pyrrole H), 6.80 (d, 1H, J=1.5 Hz, ArH), 6.72 (d, 1H, J=8 Hz, ArH), 6.69 (dd, 1H, J=8, 1.5 Hz, ArH), 5.93 (s, 2H, OCH2O), 3.89 (s, 3H, OCH3), 3.73 (s, 3H, OCH3); IR (neat film) 3348 (w, br), 2944 (w), 2890 (w), 1731 (m), 1651 (s), 1608 (s), 1503 (m), 1484 (m), 1444 (m) cm−1; HRMS (ESI) m/z: Calcd for C15H14NO6 (MH+) 304.0821; observed 304.0815.

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