Dabco → HCID 68877689, compound

Participants

Reaction Steps

DABCO (0.31 g, 2.75 mmol) in diethyl ether (11 mL) was cooled to −40° C., under nitrogen. n-Butyl lithium (2.5 M, 1.0 mL, 2.5 mmol) was added dropwise and stirred for 30 minutes. The temperature was decreased to −65° C., 3-chloropyridine (0.284 mL, 2.5 mmol) was slowly added and stirred for 30 minutes before a solution of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (0.5 g, 2.5 mmol) in diethyl ether (5 mL) was added for 30 minutes. Ammonium chloride was added and the mixture extracted into ethyl acetate, dried over sodium sulphate, filtered and the solvent removed by evaporation under vacuum. The residue was purified by flash chromatography on silica eluting with 20% ethyl acetate/cyclohexane. The fractions containing the desired product were concentrated under vacuum to give the title compound (0.18 g). LCMS m/z 313.3 [M+H]+. R.T.=4.51 min (Analytical Method 3).

Provenance & Evidence