Tetrahydrofuran → 6-[(tert-Butoxycarbonyl)methylamino]-2-pyridylethanol

Participants

Reaction Conditions

Reaction Steps

A solution of 2 N LiBH4 in THF (7 mL, 14 mmole) was added via syringe to a stirred solution of ethyl-6-[(tert-butoxycarbonyl)methylamino]-2-pyridylacetate (6.97 g, 23.7 mmole) in anhydrous THF (30 mL) under argon. The reaction was then slowly heated to reflux (initial exotherm). After 16 h at reflux, the reaction was cooled to 0° C. and carefully quenched with water (50 mL). The mixture was extracted with EtOAc (150 mL), and the organic layer was washed with brine, dried (Na2SO4), and concentrated. Purification by flash chromatography on silica gel (35% EtOAc/hexane) gave the title compound (5.26 g, 88%) as a clear oil: 1H NMR (400 MHz, CDCl3) δ 7.57 (m, 2H), 6.88 (d, J=7.2 Hz, 1H), 4.01 (t, 2H), 3.39 (s, 3H), 3.00 (t, 2H), 1.53 (s, 9H); MS (ES) m/e 253.2 (M+H)+.

Provenance & Evidence