Sodium hydride → HCID 90427717, Verbindung
Reaktionsgleichung
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][C@H:8]1[CH2:12][CH2:11][O:10][CH2:9]1)=[O:6].[H-].[Na+]>C1COCC1>[O:10]1[CH2:11][CH2:12][C@H:8]([N:7]2[CH2:2][CH2:3][NH:4][C:5]2=[O:6])[CH2:9]1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -20 °C
Versuchsvorschrift
A −20° C. solution of (S)-1-(2-chloroethyl)-3-(tetrahydrofuran-3-yl)urea (0.11 g, 0.571 mmol) in THF (6 mL) was treated with NaH (60% in mineral oil, 0.057 g, 1.428 mmol), stirred at −20° C. for 0.5 h, then at RT for 1 h. The mixture was treated with satd. NH4Cl and H2O, extracted with EtOAc (3×) and THF (2×) and the combined organics were washed with brine (1×), dried over MgSO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford (S)-1-(tetrahydrofuran-3-yl)imidazolidin-2-one (26 mg, 29%). 1H NMR (400 MHz, DMSO-d6): δ 6.32 (brs, 1 H), 4.36-4.30 (m, 1 H), 3.83-3.77 (m, 1 H), 3.63-3.53 (m, 4 H), 3.31-3.26 (m, 1 H), 3.24-3.21 (m, 2 H); 2.05-1.96 (m, 1 H); 1.84-1.76 (m, 1 H). MS (ESI) m/z: 157.1 (M+H+).