Yield:-

Reaction Conditions:

with sodium cyanoborohydride;acetic acid in methanol; pH=7; for 2 h;Inert atmosphere;

Steps:

Step 1. Nipecotic acid 5 (448 mg, 3.47 mmol) and 3-chlorobenzaldehyde (325 mg, 2.31mmol) were added to a 100-mL flask with stir bar and sealed under N2. Methanol (25mL) was added followed by sodium cyanoborohydride (2.2 g, 34.7 mmol) and acetic acid(0.265 mL, 4.62 mmol). After 2 h, the reaction was neutralized to pH 7 with saturated NaHCO3 solution and diluted with ethyl acetate (100 mL). The layers were separated and the organic layer was washed with brine (1 x 50 mL), dried over Na2SO4, filtered, and concentrated to give 1-(3-chlorobenzyl)piperidine-3-carboxylic acid 6 which was carried directly without further purification onto the next step.

References:

Germain, Andrew R.;Carmody, Leigh C.;Dockendorff, Chris;Galan-Rodriguez, Cristina;Rodriguez, Ana;Johnston, Stephen;Bittker, Joshua A.;MacPherson, Lawrence;Dandapani, Sivaraman;Palmer, Michelle;Schreiber, Stuart L.;Munoz, Benito [Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,# 23,p. 7197 - 7200] Location in patent:supporting information; experimental part