2-(Dimethylamino)ethanol → HCID 85822341, compound

Participants

Reaction Steps

To a solution of boc-glycine (1.0 g, 5.7 mmol), DCC (1.82 g, 8.84 mmol), and triethylamine (0.84 ml, 6.05 mmol) in CH2Cl2 at 0° C. was added 2-(dimethylamino)-ethanol (1.5 ml, 14.6 mmol). The mixtures were allowed to warm to room temperature. After stirring for 12 h, the solution was filtered, extracted with 1% HCl, saturated NaHCO3, water, and brine subsequently. The extracted CH2Cl2 solution was dried with anhydrous MgSO4 and evaporated to dryness. The white residue was purified by chromatography on silica gel (ethyl acetate/methanol 9:1) to give 4 (1.03 g, 74%) as a white solid; 1H NMR (C6D6, 400 MHz): 5.51 (t, 1H, J=5.90 Hz, NH), 4.01 (t, 2H, J=5.88 Hz), 3.75 (d, 2H, J=5.90 Hz), 2.22 (t, 2H, J=5.88 Hz), 1.98 (s, 6H), 1.40 (s, 9H); 13C NMR (C6D6, 100 MHz): 170.4, 156.0, 79.1, 62.8, 57.7, 45.4, 42.7, 28.4; Electrospray-ion trap-MS: Calcd for C11H22N2O4+: m/z 246.2. Found: m/Z 247.0 [M+H]+.

Provenance & Evidence