Hydrochloric Acid → HCID 86731274, compound

Temperature

70 °C

To 2-(4-(cyclopropylmethoxy)-3-fluorophenyl)-6,7-dihydro-4H-spiro[1,3-benzoxazole-5,2′-[1,3]dioxolane] (6.00 g) in a mixed solvent of THF (40 mL)-methanol (20 mL)-water (20 mL) was added 6 M hydrochloric acid (17.4 mL), and the mixture was stirred at 70° C. for 1 hr. The reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. To the organic layer was added sodium tetrahydroborate (657 mg), and the mixture was stirred at room temperature for 20 min. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (2.93 g).

1. extractionthe mixture was extracted with ethyl acetate
2. additionTo the organic layer was added sodium tetrahydroborate (657 mg)
3. stirringthe mixture was stirred at room temperature for 20 min
4. additionTo the reaction mixture was added saturated aqueous ammonium chloride solution
5. extractionthe mixture was extracted with ethyl acetate
6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
7. customthe solvent was evaporated under reduced pressure
8. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

ORD record

ord-2d3b1b4361984aa08ed342cc8109e3a1

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133129B2