Hydrochloric Acid → HCID 178461776, compound

To a solution of tert-butyl [(1S)-2-{[1-(5-bromo[1,3]oxazolo[5,4-b]pyridin-2-yl)piperidin-4-yl]oxy}-1-methylethyl]carbamate (484 mg) in THF (3 mL) was added 1.6M n-butyllithium-hexane solution (1.70 mL) at −78° C., and the mixture was stirred at the same temperature for 20 min. Trimethyl borate (0.355 mL) was added to the reaction mixture, and the mixture was allowed to warm to room temperature and stirred for 30 min. 30% Hydrogen peroxide water (3 mL) and 8M aqueous sodium hydroxide solution (1 mL) were added to the reaction mixture, and the mixture was stirred at room temperature for 30 min. The reaction mixture was neutralized with 1M hydrochloric acid, and extracted with ethyl acetate, and the extract was dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (68.1 mg).

1. stirringstirred for 30 min
2. stirringthe mixture was stirred at room temperature for 30 min
3. extractionextracted with ethyl acetate
4. dry with materialthe extract was dried over magnesium sulfate
5. customThe solvent was evaporated under reduced pressure
6. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

ORD record

ord-e243a8368f5e4c60bd2a2b178bce3c19

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08703758B2