[CH3:1][N:2]([CH2:4][C:5]1([CH3:11])[CH2:9][O:8][C:7](=[O:10])[NH:6]1)[CH3:3].[CH2:12](I)[CH2:13][CH3:14].C(=O)([O-])[O-].[K+].[K+].[ClH:22]>CCO.O.[Ag-]=O>[Cl-:22].[CH3:1][N+:2]([CH3:3])([CH2:4][C:5]1([CH3:11])[CH2:9][O:8][C:7](=[O:10])[NH:6]1)[CH2:12][CH2:13][CH3:14]A solution of 4-((dimethylamino)methyl)-4-methyloxazolidin-2-one (1.03 g, 6.51 mmol) in EtOH (5 ml) was added propyl iodide (2.5 ml, 26 mmol) in a sealed tube was heated to 50° C. for 16 h, then 70° C. for 6 h, then cooled to RT. Potassium carbonate (300 mg, 2.1 mmol) was added, and the solution was heated to 70° C. for an additional 20 h, cooled to RT, and diluted with H2O (10 ml). Silver (I) oxide (850 mg, 3.67 mmol) was added, and stirred for 30 min, and then 6.0 M HCl (˜400 ul) added until the solution was pH 7. The suspension was filtered through Celite and evaporated. ESI/APCI expected for C10H21N2O2+: 201.16. Found: 201.
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