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

Participants

Reaction Conditions

Reaction Steps

4-Amino-1-boc-piperidine (600 mg, 3.0 mmol) and triethylamine (0.417 mL, 3.0 mmol) in tetrahydrofuran (16 mL) were added to a solution of p-nitrophenylchloroformate (604 mg, 3.0 mmol) at 0° C. After 1 h, additional triethylamine was added (1.25 mL, 9 mmol) along with DL-serine methyl ester hydrochloride (571 mg, 4.79 mmol) in dimethylformamide (5 mL). The reaction was heated to 50° C. for 16 h. The mixture was concentrated and redissolved in ethyl acetate. The ethyl acetate layer was washed with 1 N sodium hydroxide solution (3×), 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 346.22 (M+1)

Provenance & Evidence