Hydrochloric Acid → (R)-methyl 2-(quinolin-8-yloxy)propanoate

Temperatur

25 °C

To a stirred mixture of quinolin-8-ol (300 mg, 2.07 mmol) in THF (5 mL) was added (S)-methyl 2-hydroxypropanoate (215 mg, 2.07 mmol), PPh3 (647 mg, 2.47 mmol) and DEAD (430 mg, 2.47 mmol). The mixture was stirred at 25° C. for 16 hours. Subsequently, 1M HCl was added (10 mL) and the solution was washed with EtOAc (20 mL×3). The pH of the aqueous solution was raised by addition of aqueous NaHCO3 (10 mL), and then this solution was washed with EtOAc (10 mL×3). The combined organic extracts were washed with brine (20 mL), dried over anhydrous Na2SO4 and concentrated. The residue was purified by silica column chromatography to afford the product as a colorless oil (300 mg, 62.5% yield). LCMS (m/z): 233.1 [M+H]+

1. washthe solution was washed with EtOAc (20 mL×3)
2. temperatureThe pH of the aqueous solution was raised by addition of aqueous NaHCO3 (10 mL)
3. washthis solution was washed with EtOAc (10 mL×3)
4. washThe combined organic extracts were washed with brine (20 mL)
5. dry with materialdried over anhydrous Na2SO4
6. concentrationconcentrated
7. customThe residue was purified by silica column chromatography

ORD-Eintrag

ord-dc7f0f36f25c4ba48ddd3550370545fb

Quelldatensatz

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08940726B2