Tetrabutylammonium Fluoride → (S)-3-ethoxy-2-hydroxy-N-(5-methylpyridin-2-yl)propanamide

Participants

Reaction Steps

A solution of tetrabutylammonium fluoride (1M in THF) (3.25 mL, 3.25 mmol) was added in one portion to a stirred solution of (S)-2-(tert-butyldimethylsilyloxy)-3-ethoxy-N-(5-methylpyridin-2-yl)propanamide (Intermediate G2) (1.1 g, 3.25 mmol) in tetrahydrofuran (25 mL). The resulting solution was stirred at ambient temperature for 4 hours. The reaction mixture was concentrated and diluted with EtOAc (50 mL) washed sequentially with water (20 mL) and saturated brine (20 mL). The organic layer was dried (MgSO4) and evaporated. The residue was purified by flash silica chromatography, elution gradient 50 to 100% EtOAc in isohexane to afford (2S)-3-ethoxy-2-hydroxy-N-(5-methylpyridin-2-yl)propanamide (730 mg, 100%). 1H NMR (400 MHz, CDCl3) δ 1.24 (3H, t), 2.30 (3H, s), 3.60 (2H, q), 3.76-3.79 (2H, m), 3.87 (1H, s), 4.33-4.38 (1H, m), 7.52 (1H, dd), 8.11-8.13 (2H, m), 9.20 (1H, s); m/z (ESI+) (M+H)+=225; HPLC tR=0.96 min.

Provenance & Evidence