1-(3-methoxypropyl)imidazolidin-2-one

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 0° C. solution of 1-(2-chloroethyl)-3-(3-methoxypropyl)urea (0.300 g, 1.541 mmol) in THF (8 mL), under Ar, was treated with NaH (60% in mineral oil, 0.154 g, 3.85 mmol) allowed to warm to RT and stirred. The mixture was cooled to 0° C., treated slowly with satd. NH4Cl, then brine, warmed to RT and stirred for 10 min. The layers were separated, the aqueous layer extracted with EtOAc (2×) and the combined organics were dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford 1-(3-methoxypropyl)imidazolidin-2-one (214 mg, 88%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 6.21 (s, 1 H), 3.31-3.24 (m, 4 H), 3.21-3.15 (m, 5 H), 3.06-3.01 (m, 2 H), 1.66-1.58 (m, 2 H); MS (ESI) m/z: 159.1 (M+H+). The mixture was cooled to 0° C. treated slowly with satd stirred for 10 min The layers were separated the aqueous layer extracted with EtOAc (2×) the combined organics were dried over Na2SO4 concentrated to dryness purified via silica gel chromatography (MeOH/DCM)