Tetrahydrofuran → Methyl N-{[(1-(tert-butoxycarbonyl)piperidin-4-yl)amino]carbonyl}glycinate

Participants

Reaction Steps

4-Amino-1-boc-piperidine (964 mg, 4.8 mmol) in tetrahydrofuran (15 mL) was added to a solution of p-nitrophenylchloroformate (970 mg, 4.8 mmol) and triethylamine (0.67 mL, 4.8 mmol) in tetrahydrofuran (15 mL) at 0° C. After 1 h, additional diisopropylethylamine was added (1.3 mL, 9.6 mmol) along with glycine methyl ester hydrochloride (604 mg, 4.8 mmol). The reaction was warmed to room temperature and stirred overnight. The mixture was filtered, concentrated and redissolved in ethyl acetate. The ethyl acetate layer was washed with 1N sodium hydroxide (3×), saturated sodium bicarbonate solution, water, brine, and dried over sodium sulfate. Purification by silica gel chromatography (100% dichloromethane→8% methanol {1% ammonium hydroxide}/dichloromethane) gave the title compound (700 mg). MS 400.29 (M+1)

Provenance & Evidence