Dimethyl Sulfoxide → HCID 86731566, compound

Participants

Reaction Conditions

Reaction Steps

A solution of DMSO (1.75 mL, 24.7 mmol) in CH2Cl2 was cooled at −78° C. and treated with oxalyl chloride (2.16 mL, 24.7 mmol) dropwise. The solution was stirred at −78° C. for 20 mins and then treated with a solution of [(3R,6R)-1-(4-methoxybenzyl)-6-methylpiperidin-3-yl]methanol (4.10 g, 16.4 mmol) in CH2Cl2 (15 mL) dropwise. After stirring at −78° C. for 1 h, the reaction was allowed to warm to ambient temperature and triethylamine (11.5 mL, 82.0 mmol) was added. After stirring overnight, the reaction was diluted with CH2Cl2 and washed with water and brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was purified by silica gel flash chromatography eluting with 0-10% MeOH in CH2Cl2 to provide (3R,6R)-1-(4-methoxybenzyl)-6-methylpiperidine-3-carbaldehyde as an orange oil, which gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 266.4 for M+H3O+.

Provenance & Evidence