Tetrahydrofuran → HCID 68568949, compound

Participants

Reaction Steps

4-Amino-1-boc-piperidine (770 mg, 3.85 mmol) and triethylamine (0.536 mL, 3.85 mmol) in tetrahydrofuran (5 mL) was added to a solution of p-nitrophenylchloroformate (775 mg, 3.85 mmol) in tetrahydrofuran (15 mL) at 0° C. After 1 h, additional triethylamine was added (1.07 mL, 7.7 mmol) along with methyl O-[tert-butyl(diphenyl)silyl]serinate (1.38 g, 3.85 mmol). The reaction warmed to ambient temperature and was then heated to 50° C. After 16 h, the mixture was concentrated and redissolved in ethyl acetate. The ethyl acetate layer was washed with saturated sodium bicarbonate 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 (1.8 g). MS 584.62 (M+1)

Provenance & Evidence