2-(Dimethylamino)ethanol → HCID 86601379, compound

Participants

Reaction Steps

To a suspension of compound 129 (1.00 g, 2.04 mmol) in THF (6.8 mL) at room temperature under N2 atmosphere were successively added N,N-dimethylethanolamine (225 μL, 2.24 mmol) and triphenylphosphine (696 mg, 2.65 mmol) followed by diisopropyl azodicarboxylate (550 μL, 2.65 mmol). Heat was evolved and the mixture turned dark red. It was stirred for 4 h, THF was removed in vacuo and the dark residue was partitioned between EtOAc and H2O. Organic phase was collected and extracted with HCl 1N. Acidic extract was separated and neutralized with saturated aqueous NaHCO3 under vigorous stirring. A white precipitate was formed which was collected by filtration to afford the title compound 133 (430 mg, 37% yield). 1H NMR: (acetone-d6) δ(ppm): 7.99 (d, J=8.4 Hz, 2H), 7.70 (dd, J=8.0, 2.2 Hz, 1H), 7.59 (d, J=8.4 Hz, 2H), 7.56 (d, J=1.6 Hz, 1H), 7.33 (d, J=9.0 Hz, 1H), 7.27 (d, J=2.5 Hz, 1H), 7.19 (quint.d, J=7.8, 2.4 Hz, 2H), 6.87 (dd, J=8.8, 2.5 Hz, 1H), 4.80 (s, 2H), 4.08 (t, J=5.9 Hz, 2H), 2.67 (t, J=5.7 Hz, 2H), 2.27 (s, 6H), 1.48 (s, 9H). m/z: 562.5 (MH+).

Provenance & Evidence