Pyridine → HCID 67264998, compound

Participants

Reaction Steps

Add thionyl chloride (1.2 equiv; 10.5 mmol; 765 μL) dropwise over 3 min at 20° C. to a solution of piperidine-1,4-dicarboxylic acid mono-tert-butyl ester (1.00 equiv; 8.75 mmol; 2.03 g) and pyridine (5 equiv; 43.74 mmol; 3.54 mL) in DCM (60 mL). Stir 90 min. Add (R)-3-[2-(4-fluoro-3-trifluoromethyl-phenyl)-2-oxo-ethylamino]-piperidine-1-carboxylic acid benzyl ester hydrochloride (0.80 equiv; 7.00 mmol; 3.32 g) followed by TEA (3.5 equiv; 30.62 mmol; 4.3 mL) dropwise over 3 min and stir 18 h. Wash the organic phase 3× with 1N HCl, water, brine, dry over MgSO4, filter and evaporate. Purify the residue on 150 g silica gel with 20-50% EA/DCM to provide the title compound (2.86 g; 4.41 mmol; 50%). MS (ES+): m/z=672 (M+Na).

Provenance & Evidence