Hydrochloric Acid → HCID 71233198, compound

Participants

Reaction Steps

To a solution of (S)-tert-butyl 3-(benzyloxycarbonylamino)-3-methylpiperidine-1-carboxylate (3.5 g, 10.04 mmol) in dioxane (14 mL) was added 4N HCl in dioxane (15 mL, 60 mmol) drop wise at 0° C. The resultant clear solution was stirred at room temperature for 2 h. The reaction mixture was concentrated, the pale yellow foam was dissolved in water (50 mL), washed with ethyl acetate (2×30 mL), the aqueous layer was basified with saturated NaHCO3 (until reach pH ˜9) at 0° C. The resultant aqueous layer was extracted with CHCl3 (3×50 mL), the combined organic extracts was washed with water (50 mL), brine (10 mL), dried (Na2SO4), concentrated and dried in high vacuum to get the product (S)-benzyl (3-methylpiperidin-3-yl)carbamate (2.45 g, 9.85 mmol, 98% yield) as a light yellow solid. Anal. Calcd. for C14H20N2O2 m/z 248.3, found: 249.2 (M+H)+; 1H NMR (400 MHz, CD3OD) δ ppm 7.42-7.26 (m, 5 H), 5.13-4.97 (m, 2 H), 3.20 (d, J=13.2 Hz, 1 H), 2.93-2.82 (m, 1 H), 2.60-2.50 (m, 2 H), 2.13 (d, J=13.0 Hz, 1 H), 1.69-1.56 (m, 1 H), 1.54-1.37 (m, 2 H), 1.27 (s, 3 H).

Provenance & Evidence