Hydrochloric Acid → 1-[(Tert-butyl)oxycarbonyl]-3-(4-chlorobenzyl)piperidine-3-carboxylic acid

Participants

Reaction Steps

A suspension of Ethyl-3-(4-chlorobenzyl)-N-Boc-piperidin-3-carboxylate (36.4 g, 0.105 mol) in isopropyl alcohol (300 mL) was treated with 10 N NaOH (300 mL). The mixture was heated at reflux for 48 hours. The reaction was cooled to room temperature and carefully neutralized by pouting over 1 L of crushed ice and adding 6 N HCl until pH 3. The mixture was then extracted with ethyl acetate (3×500 mL). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated at reduced pressure to give 31 g of the product.

Provenance & Evidence