4-Piperidinecarboxylic acid → HCID 61800653, compound

Participants

Reaction Steps

Isopropyl chloroformate (1.0M in toluene, 55 mL, 55 mmol) was added dropwise to a mixture of 4-piperidinecarboxylic acid (6.5 g, 50 mmol) and sodium hydroxide (4.4 g, 110 mmol) in water (25 mL) at ambient temperature. The mixture was stirred at ambient temperature overnight. The aqueous phase was separated and adjusted to pH=1 with concentrated HCl. The aqueous phase was extracted with EtOAc, and the organics were dried over MgSO4, filtered, and the filtrate was concentrated to give 10.2 g (95%) of 1-{[(1-methylethyl)oxy]carbonyl}-4-piperidinecarboxylic acid as a white solid. 1H NMR (400 MHz, CDCl3): δ 4.89 (septet, 1H, J=6.2 Hz), 4.04 (d, 2H, J=3.9 Hz), 2.97-2.79 (m, 2H), 2.58-2.38 (m, 1H), 2.00-1.80 (m, 2H), 1.72-1.53 (m, 2H), 1.21 (d, 6H, J=6.3 Hz); LRMS (ESI), m/z 214 (M−H).

Provenance & Evidence