Potassium Carbonate → tert-butyl [(1S)-2-({1-[6-(2-cyclopropylethoxy)-1,3-benzoxazol-2-yl]piperidin-4-yl}oxy)-1-methylethyl]carbamate

To a solution of 2-cyclopropylethanol (550 mg) in THF (10 mL) were added triethylamine (0.80 mL) and methanesulfonyl chloride (0.50 mL), and the mixture was stirred at room temperature for 30 min. The reaction mixture was added to a suspension of tert-butyl [(1S)-2-{[1-(6-hydroxy-1,3-benzoxazol-2-yl)piperidin-4-yl]oxy}-1-methylethyl]carbamate (250 mg) and potassium carbonate (1.8 g) in DMF (10 mL), and the mixture was stirred at room temperature for 15 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (190 mg).

1. stirringthe mixture was stirred at room temperature for 15 hr
2. washwashed with saturated brine
3. dry with materialdried over anhydrous magnesium sulfate
4. customThe solvent was evaporated under reduced pressure
5. customthe obtained residue was purified by silica gel chromatography (hexane/ethyl acetate)

ORD record

ord-59c8b7366b874bbdaebd2bf7df6eacb3

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08703758B2