Diisopropylamine → HCID 22959069, compound

Participants

Reaction Steps

To a mixture of diisopropylamine (280 μl; 1.99 mmol; 1 eq) and boc-beta-alanine (414.7 mg; 2.19 mmol; 1.10 eq) in DCM (30 ml), are added triethylamine (829 μl; 5.98 mmol; 3 eq) and 2-chloro-1-methylpyridinium iodide (1 527 mg; 5.98 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 layers are 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 compound is isolated as a slightly yellow solid (511.2 mg; 94%).

Provenance & Evidence