Water → HCID 57504576, compound

Participants

Reaction Steps

n-BuLi (3.40 mL, 1.6 M in hexanes, 5.44 mmol) was added slowly to a stirred solution of 2-amino-5-picoline (616 mg, 5.70 mmol) in anhydrous THF (8 mL). The reaction mixture was kept at ambient temperature for 10 minutes before a solution of ethyl (2S)-2-{[tert-butyl(dimethyl)silyl]oxy}-4-(dimethylamino)butanoate (Step 2) (1.50 g, 5.18 mmol) in anhydrous THF (2 mL) was added. The reaction mixture was stirred at ambient temperature for 1 h. Water and EtOAc were added and the two phases were separated. The aqueous phase was extracted with EtOAc. The organic extracts were combined and washed with water, dried over MgSO4 and concentrated in vacuo. The residue was purified with column chromatography (silica gel, eluting with EtOAc) to give the title compound (320 mg), 1H NMR (300 MHz, CDCl3) δ 8.89 (br s, 1H), 8.12 (m, 2H), 7.51 (dd, 1H), 4.32 (t, 1H), 2.47 (m, 1H), 2.31 (m, 4H), 2.21 (s, 6H), 1.97 (m, 2H), 0.98 (s, 9H), 0.15 (d, 6H).

Provenance & Evidence