Acetic Acid → 4-((5-Bromopyridin-2-yl)methyl)morpholine

Participants

Reaction Steps

Sodium triacetoxyborohydride (1.6 gm, 7.5 mmol) was added to a solution of 5-bromopicolinaldehyde (1.0 g, 5.4 mmol) and morpholine (0.54 g, 6.2 mmol) in 1,2-dichloroethane (10 mL) and this was left stirring for 2 hr. Acetic acid (0.35 mL, 6.2 mmol) was added and the reaction was left stirring over the weekend. It was diluted with EtOAc and washed with sat. aq. NaHCO3 followed by brine. This was concentrated, captured on a SCX column, washed with MeOH, and released with 2 N NH3 in MeOH to give 4-((5-bromopyridin-2-yl)methyl)morpholine (537 mg, 2.09 mmol, 39% yield) as a brown oil. MS (ESI) m/z 256.96 (M+H). 1H NMR (500 MHz, chloroform-d) δ ppm 8.61 (1H, d, J=2.44 Hz), 7.77 (1H, dd, J=8.24, 2.44 Hz), 7.33 (1H, d, J=8.24 Hz), 3.67-3.77 (4H, m), 3.60 (2H, s), 2.42-2.57 (4H, m).

Provenance & Evidence