1-[(TERT-BUTYL)OXYCARBONYL]-3-(4-CHLOROBENZYL)PIPERIDINE-3-CARBOXYLIC ACID synthesis

Yield:-

Reaction Conditions:

with hydrogenchloride;sodium hydroxide

Steps:

2.B N-boc-3-(4-chlorobenzyl)piperidin-3-carboxylic acid
Step B N-boc-3-(4-chlorobenzyl)piperidin-3-carboxylic acid 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. ¹ H NMR CDCl₃ δ10.18 (br s), 7.26 (d, J=8.5 Hz, 2H), 7.04 (d, J=8.5 Hz, 2H), 3.95 (m, 1H), 3.6 (m, 1H), 3.2 (m, 2H), 2.90 (d, J=12 Hz, 1H), 2.78 (d, J =12 Hz, 1H), 2.00 (m, 1H), 1.75-1.30 (m, 3H), 1.44 (s, 9H).

References:

Merck & Co., Inc. US5475109, 1995, A