4-Piperidinecarboxylic acid → 1-Carbobenzoxy-4-piperidinecarboxylic Acid

Participants

Reaction Steps

To a slurry of 66.4 g (0.50 mol) of isonipecotic acid, and 145 mL (0.50 mol) of triethylamine in 600 mL of methylene chloride was added a solution of 72 mL (0.50 mol) of benzyl chloroformate in 200 mL of toluene at 10° C. The slurry was allowed to warm to room temperature and after stirring for 17 h was treated with 1 L of a 10% aqueous sodium carbonate solution. The layers were separated, and the aqueous portion was extracted once with ether and then acidified to pH 3. The aqueous portion was then extracted with methylene chloride. The organic extract was washed with brine, dried over MgSO4 and concentrated to give 35.2 g of the title compound as an oil which was used without further purification.

Provenance & Evidence