5,6,7,8-Tetrahydro-1,8-naphthyridine-2-carbaldehyde → (5,6,7,8-Tetrahydro-1,8-naphthyridin-2-yl)methanol

Participants

Reaction Conditions

Reaction Steps

A mixture of 5,6,7,8-tetrahydro-[1,8]naphthyridine-2-carboxaldehyde 1 (0.5 g) and lithhiumborohydride (3.0 mL, 2.0 M) in THF (5.0 ML) was stirred at 5° C. for 1 h. The reaction mixture was then allowed to warm to room temperature over a period of another hour, quenched with acetic acid (2.0 mL) and concentrated under reduced pressure. The residue was partitioned between 1N NaOH (20.0 mL)and EtOAc (25 mL). The organic phase was washed with brine (2×0 mL), dried (Na2SO4), and concentrated to dryness. The resulting residue was purified by silica gel flash chromatography using EtOAc containing 10% methanol to give 0.3 g of the title compound as a pale yellow solid: 1H-NMR δ (CD3OD) 7.18 (d, 1H, J=7.6 Hz), 6.58 (d, 1H, J=7.6 Hz), 4.40 (s, 2H), 3.34 (m, 2H), 2.69 (t, 2H, J=6.0 Hz), 1.85 (t, 2H, J=6.0 Hz); ES-MS, m/z =165 (MH+).

Provenance & Evidence