Ethyl Acetate → 6-((Tert-butyldiphenylsilyloxy)methyl)-4-methylpyridin-3-amine

Participants

Reaction Steps

To a solution of 2-((tert-butyldiphenylsilyloxy)methyl)-4-methyl-5-nitropyridine (1.5 g, 3.7 mmol) in 20 ml of sat. NH4Cl, were added zinc (1.7 g, 26 mmol) portionwise at 0° C. for 10 min. The reaction was stirred at the same temperature for 1 hr. The reaction was added with ethyl acetate (20 mL) and stirred for additional 1 hr. The organic layer was taken up, washed with H2O, and dried over MgSO4. The ethyl acetate was concentrated under vacuum to afford 6-((tert-butyldiphenylsilyloxy)methyl)-4-methylpyridin-3-amine in 72% (1.0 g). The compound was used for the next step without further purification. 1HNMR (CDCl3, 400 MHz) δ 1.10 (s, 9H), 2.21 (s, 3H), 4.64 (s, 2H), 5.01˜5.13 (b, 2H), 7.12 (s, 1H), 7.31˜7.71 (m, 10H), 7.89 (s, 1H). Exact mass calculated for C23H28N2OSi 376.57 found 377.4 (MH+).

Provenance & Evidence