Reaktion #1555911

Reaktionsgleichung

Triethylamine

53

6-Chloro-2,2-Dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one

aziridine

2-Benzo[1,3]dioxol-5-yl-aziridine

→

54

Ausbeute 85.0%

6-(2-Benzo[1,3]dioxol-5-yl-aziridin-1-yl)-2,2-Dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one

Ausbeute 85.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe crude reaction mixture
2. 2
   Sonstigepurified by silica gel column chromatography (1% triethylamine and 49% benzene in ethyl acetate)

Vorschrift

Triethylamine (0.4 mL, 3.0 mmol, 2.0 equiv) and 13-chloroenone 53 (280 mg, 1.5 mmol, 1.0 equiv) were sequentially added to a stirred solution of aziridine 15 (360 mg, 2.2 mmol, 1.5 equiv) in tetrahydrofuran (10 mL) at 25° C. The resulting white mixture was stirred at 25° C. for 3 h. The crude reaction mixture was loaded directly onto a column and purified by silica gel column chromatography (1% triethylamine and 49% benzene in ethyl acetate) to afford 54 (400 mg, 85% yield) as a yellow foam. Rf=0.68 (1% triethylamine and 49% benzene in ethyl acetate); 1H NMR (500 MHz, C6D6) δ 6.55-6.70 (m, 3H, ArH), 5.24-5.28 (m, 2H, OCH2O), 5.14-5.18 (m, 1H, NCCH), 4.50-4.56 (m, 1H, CH(OR)), 4.19-4.27 (m, 1H, CH(OR)), 2.46-3.18 (m, 1H, ArCHN), 1.84-2.17 (m, 1H, CH2N), 1.63-1.78 (m, 1H, CH2N), 1.28-1.32 (m, 3H, CH3), 1.10-1.12 (m, 3H, CH3); IR (neat film) 2989 (w), 1703 (m), 1586 (s) cm−1; HRMS (ESI) m/z: Calcd for C17H18NO5 (MH+) 316.1185, observed 316.1186.

Quelle