Triethylamine → Tert-butyl [3-(4,4-dimethyl-1,3-oxazolidin-3-yl)-3-oxopropyl]carbamate

Participants

Reaction Steps

To a mixture of 4,4-dimethyloxazolidine (287 μl; 2 mmol; 1 eq) and boc-beta-alanine (416.3 mg; 2.2 mmol; 1.10 eq) in DCM (30 ml), are added triethylamine (832 μl; 6 mmol; 3 eq) and 2-chloro-1-methylpyridinium iodide (1533 mg; 6 mmol; 3 eq). The mixture is stirred for 2 days at RT. The reaction is followed by TLC cyclohexane/EtOAc 1:1). The reaction mixture is then washed twice with NH4Cl sat. solution and twice with NaHCO3 sat. solution. The organic layer is dried over Na2SO4, filtered and concentrated to give 760 mg of an orange oil, which is purified by flash chromatography (cyclohexane/EtOAc gradient, from 9/1 to 1/1 over 30 min). The title product is isolated as a white-off solid (420.5 mg; 77%).

Provenance & Evidence