Water → 6-(Methylamino)-2-pyridylethanol

Participants

Reaction Steps

A solution of 1.0 M LiAlH4 in THF (95 mL, 95 mmole) was added dropwise to a mechanically stirred suspension of ethyl-2-(methylamino)-6-pyridylacetate (7.34 g, 31.82 mmole) in dry THF (64 mL) at 0° C. under argon. The addition was done slowly until gas evolution subsided, then the remaining solution was added rapidly. Addition required 5-7 min. The reaction was warmed to RT and stirred for 45 min, then was heated to reflux. After 10 min, the reaction was cooled to 0° C. and worked up by sequential dropwise addition of H2O (3.6 mL), 15% NaOH (3.6 mL), and H2O (10.8 mL). The mixture was stirred for 15 min at 0° C. and 15 min at RT, then was filtered through a Buchner funnel. The filter pad was washed with plenty of THF, and the filtrate was concentrated. The residue was reconcentrated from toluene, then was chromatographed on silica gel (5% MeOH in 1:1 EtOAc/CHCl3) to afford the title compound (3.23 g, 67%) as a yellow oil which solidified to a waxy solid: 1H NMR (250 MHz, CDCl3) δ7.36 (dd, J=8.3, 7.3 Hz, 1 H), 6.42 (d, J=7.3 Hz, 1 H), 6.26 (d, J=8.3 Hz, 1 H), 4.93-5.28 (m, 1 H), 4.38-4.60 (m, 1 H), 3.96 (t, J=5.4 Hz, 2 H), 2.90 (d, J=5.2 Hz, 3 H), 2.84 (t, J=5.4 Hz, 2 H); MS (ES) m/e 153 (M+H)+.

Provenance & Evidence