(4-Aminomethyl-pyridin-2-yl)-carbamic acid tert-butyl ester

Synthesis

856897-86-4

639091-78-4

The general procedure for the synthesis of 2-(BOC-amino)-4-(aminomethyl)pyridine from the compound (CAS: 856897-86-4) is as follows:(b) Preparation of tert-butyl (4-aminomethylpiperidin-2-yl)carbamate; a solution of sodium borohydride (0.92 g, 24 mmol) in water (25 mL) was added to a Pd/C slurry (10%, 50% wet weight) , water (25 mL) was added with stirring, followed by rapid dropwise addition of a solution of tert-butyl (4-azidomethylpyridin-2-yl)carbamate (0.40 g, 6.1 mmol; see step (a) above) in THF (75 mL), and the reaction was carried out under cooling in an ice bath. The reaction mixture was stirred at room temperature for 4 h, followed by the slow addition of aqueous sodium bisulfate to an acidic pH. The reaction mixture was filtered by pumping through a Celite pad and washed with water. The combined aqueous layers were washed with ethyl acetate, adjusted to an alkaline pH by addition of aqueous NaOH and extracted with ethyl acetate (3×). The combined organic phases were washed with water, dried (Na2SO4), filtered and the solvent evaporated under reduced pressure. The crude product (1.1 g, 85% yield) was crystallized and used without further purification.1H NMR (300 MHz, CDCl3) δ 10.06 (m, 1H), 8.55 (m, 1H), 7.94 (m, 1H), 6.88 (m, 1H), 3.83 (bs, 2H), 1.50 (s, 9H).

References