Hydrochloric Acid → HCID 57541884, compound

Methyl (S)-4-[(2,3-dihydro-1H-inden-1-yl) oxy]benzenepropanoate (4.4 g, 15 mmol) was dissolved in methanol (50 mL), 1N aqueous sodium hydroxide solution (25 mL) was added and the mixture was stirred at room temperature for 18.5 hrs. 1N Hydrochloric acid (25 mL) was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over sodium sulfate. The mixture was concentrated under reduced pressure and the obtained crystals were washed with hexane to give colorless crystals (4.2 g, 96% ee). The crystals were recrystallized from a mixed solvent of diisopropyl ether (70 mL) and hexane (70 mL) to give the title compound (2.3 g, 99.4% ee, yield 56%) as colorless crystals. As the secondary crystals, 0.67 g (yield 16%, 97% ee) of the title compound was obtained and as the tertiary crystals, 0.16 g (yield 4%, 92% ee) of the title compound was obtained.

1. extractionthe mixture was extracted with ethyl acetate
2. washThe organic layer was washed with saturated brine
3. dry with materialdried over sodium sulfate
4. concentrationThe mixture was concentrated under reduced pressure
5. washthe obtained crystals were washed with hexane
6. customto give colorless crystals (4.2 g, 96% ee)
7. customThe crystals were recrystallized from a mixed solvent of diisopropyl ether (70 mL) and hexane (70 mL)

ORD record

ord-791885cb1a9c444392fbcbaf197f64ed

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07960369B2