Potassium Carbonate → HCID 118114006, compound

To a stirred solution of tert-butyl 4-hydroxy-3-methoxybenzylcarbamate (21.02 g, 82.99 mmol) in acetonitrile (250 mL) was added potassium carbonate (30.61 g, 221.5 mmol) and 5-(chloromethyl)-2-methylpyridine hydrochloride (16.25 g, 91.29 mmol). The resulting mixture was heated to reflux. After 63 h, the brown suspension was allowed to cool to room temperature and was diluted with water (1000 mL). The mixture was extracted with dichloromethane (3×250 mL). The combined organic phases were dried over magnesium sulfate, filtered, and concentrated to provide 31.59 g (>100%) of tert-butyl 3-methoxy-4-((6-methylpyridin-3-yl)methoxy)benzylcarbamate as a brown oil.

1. temperatureThe resulting mixture was heated to reflux
2. extractionThe mixture was extracted with dichloromethane (3×250 mL)
3. dry with materialThe combined organic phases were dried over magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated

ORD record

ord-7a37e65cf4ce490ba4586ebcc21347a1

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09174986B2