3-Amino-1-propanol → HCID 59332899, compound

Participants

Reaction Steps

Diisopropyl azodicarboxylate (4.65 mL, 24 mmol) was added slowly to a dioxane (200 mL) solution of 2-bromo-pyridin-3-ol (3.50 g, 20 mmol), 3-aminopropanol (1.67 mL, 22 mmol) and triphenylphosphine (6.30 g, 24 mmol) at 10° C. After stirring the mixture for 30 mm at this temperature, it was refluxed for 18 h Upon cooling, the volatiles were evaporated and the residue was purified fey chromatography (silica, 3% MeOH in CH2Cl2 then 5% (2M NH3, m MeOH) in CH2Cl2 to afford the title compound (3.19 g, 69%). 1H NMR (300 MHz, CDCl3, δ): 7.98 (dd, J=4.5, 1.8 Hz, 1H), 7.23 (dd, J=4.5, 8.2 Hz, 1H), 7.15 (dd, J=1.8, 8.2 Hz, 1H), 4.15 (t, J=6.0 Hz, 2H), 2.98 (t, J=6.6 Hz, 2H), 2.00 (m, 2H). MS (ESI); m/e 231 and 233(M+H)+.

Provenance & Evidence