Water → HCID 9839330, compound

Participants

Reaction Steps

1-(tert-Butoxycarbonyl)-4-[2,2-di(ethoxycarbonyl)ethyl]piperidine (12.2 g, 34 mmol), prepared as in Example 1, Step (b), and potassium hydroxide (4.2 g, 75 mmol) were combined in ethanol (10 mL), THF (20 mL), and water (50 mL) and the mixture was heated at reflux for 3 hours. The mixture was cooled and washed with ether, acidified with sulfuric acid, and extracted into ether. The ether was dried over sodium sulfate and evaporated. Crystallization of the residue from ether gave 1-(tert-butoxycarbonyl)-4-[2,2-di(carboxy)ethyl]piperidine (8.5 g, 28 mmol) which was heated in an oil bath to 165° C. until evolution of CO2 ceased (approximately 10 minutes). The residue was cooled and upon crystallization gave 3-[l-(tert-butoxycarbonyl)piperidin-4-yl]propionic acid (7.2 g, 28 mmol), m.p. 81°-83° C.

Provenance & Evidence