Dimethyl Sulfoxide → HCID 86731566, compound

Temperature

-78 °C

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+.

1. stirringAfter stirring at −78° C. for 1 h
2. temperatureto warm to ambient temperature
3. stirringAfter stirring overnight
4. washwashed with water and brine
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe crude material was purified by silica gel flash chromatography
9. washeluting with 0-10% MeOH in CH2Cl2

ORD record

ord-70bf07b937c84e3f9493bdae739f8977

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08940898B2