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

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.

1. concentrationThe reaction mixture was concentrated
2. additiondiluted with EtOAc (50 mL)
3. washwashed sequentially with water (20 mL) and saturated brine (20 mL)
4. dry with materialThe organic layer was dried (MgSO4)
5. customevaporated
6. customThe residue was purified by flash silica chromatography, elution gradient 50 to 100% EtOAc in isohexane

ORD-Eintrag

ord-3bba3ec54266444eb9cb3109c1da6110

Quelldatensatz

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08143263B2