Potassium Carbonate → HCID 86731563, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of potassium carbonate (0.556 g, 4.02 mmol) and dimethyl (1-diazo-2-oxopropyl)phosphonate (0.837 g, 4.36 mmol) in methanol (35 mL) under an atmosphere of nitrogen was cooled to 0° C. To this mixture was added a solution of (3R,6R)-6-methyl-1-{[2-(2H-1,2,3-triazol-2-yl)phenyl]carbonyl}piperidine-3-carbaldehyde (1.00 g, 3.35 mmol) in methanol (12 mL) dropwise. The reaction was allowed to warm slowly to RT and stir for 17 h. The mixture was concentrated in vacuo, treated with water, and extracted with ethyl acetate. The organic fraction was washed with water and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The resultant residue was purified via silica gel chromatography eluting with 0-50% ethyl acetate in hexanes to provide [(2R,5S)-5-ethynyl-2-methylpiperidin-1-yl][2-(2H-1,2,3-triazol-2-yl)phenyl]methanone which gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 295.3 for M+H+, and [(2R,5R)-5-ethynyl-2-methylpiperidin-1-yl][2-(2H-1,2,3-triazol-2-yl)phenyl]methanone which gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 295.2 for M+H+.

Provenance & Evidence