Triethylamine → Cyclopropylmethyl 2,5-dioxopyrrolidin-1-yl carbonate

Reaktionsgleichung

[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.[C:6](=O)([O:15]N1C(=O)CCC1=O)[O:7][N:8]1[C:12](=[O:13])[CH2:11][CH2:10][C:9]1=[O:14].C(N(CC)CC)C>C(#N)C>[C:6](=[O:15])([O:7][N:8]1[C:12](=[O:13])[CH2:11][CH2:10][C:9]1=[O:14])[O:5][CH2:4][CH:1]1[CH2:3][CH2:2]1

Komponenten

Versuchsvorschrift

To a stirred solution of cyclopropylmethanol (1.0 g, 13.8 mmol) in acetonitrile (15 mL) was added bis(2,5-dioxopyrrolidin-1-yl) carbonate (7.1 g, 27.7 mmol) and triethylamine (5.8 mL, 41.6 mmol). The reaction was stirred overnight then quenched with saturated NaHCO3 (aq.) and extracted with ethyl acetate (3×50 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to provide the title compound as an amber oil: 1H NMR (300 MHz, CDCl3) δ 4.16 (d, J=7.5 Hz, 2H), 2.84 (s, 4H), 1.26 (m, 1H), 0.70-0.64 (m, 2H), 0.40-0.35 (m, 2H).