Potassium Carbonate → HCID 86731568, compound

Participants

Reaction Steps

A mixture of (3R,6R)-1-(4-methoxybenzyl)-6-methylpiperidine-3-carbaldehyde (3.01 g, 12.2 mmol) and potassium carbonate (3.36 g, 24.3 mmol) in MeOH (150 mL) was treated with dimethyl (1-diazo-2-oxopropyl)phosphonate (2.19 mL, 14.6 mmol) and allowed to stir at ambient temperature for 3 d. The reaction was concentrated in vacuo and the residue taken up in sated, aqu. NaHCO3 and extracted twice with EtOAc. The organics were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo, providing (2R,5S)-5-ethynyl-1-(4-methoxybenzyl)-2-methylpiperidine as an orange oil. The material gave a mass ion (ES+) of 244.2 for M+H+. 1H NMR δ (ppm) (CDCl3): 7.21 (2H, dm J=8.4 Hz), 6.83-6.87 (2H, m), 3.98 (2H, d, J=13.4 Hz), 3.80 (3H, s), 3.11 (1H, d, J=13.6 Hz), 3.11 (1H, s), 2.91-2.96 (1H, m), 2.39-2.44 (1H, m), 2.18-2.25 (1H, m), 1.89-1.98 (2H, m), 1.64-1.69 (2H, m), 1.31-1.40 (2H, m), 1.18 (3H, d, J=6.0 Hz).

Provenance & Evidence