Hydrochloric Acid → (S)-tert-butyl 1-oxo-1-(quinolin-3-yl)propan-2-ylcarbamate

Temperatur

-10 °C

(S)-tert-butyl 1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate (2.5 g, 10.76 mmol) was suspended in THF (5 mL) and stirred at −10° C., isopropylmagnesium chloride 2.0M solution in THF (5.4 ml, 10.80 mmol) was added and a solution was formed. To this solution was added a solution of Lithium tri(3-quinolinyl)magnesiate in THF/Hexane, prepared from 3-bromoquinoline (1.471 ml, 10.81 mmol) according to the procedure described by Sylvain Dumouchel et-al. in Tetrahedron 59 (2003) 8629-8640. The mixture was stirred at −10° C. for 30 minutes and was the allowed to reach room temperature and stirred over night, 15 h. The reaction mixture, a clear red solution, was slowly poured into ice-cooled 1M HCl (aq) (100 mL). EtOAc (150 mL) was added and the mixture was stirred for a few minutes, the water phase was extracted once with EtOAc, the combined EtOAc solutions was further washed with saturated NaHCO3 (aq) and brine. The crude material was purified by flash-chromatography on silica using a gradient of 0% to 40% EtOAc in Heptane. The obtained material was the further purified by HPLC to afford the subtitle compound as a yellow sticky oil. Yield 1.6 g (49%)

1. customa solution was formed
2. stirringThe mixture was stirred at −10° C. for 30 minutes
3. customto reach room temperature
4. stirringstirred over night, 15 h
5. additionThe reaction mixture, a clear red solution, was slowly poured into ice-
6. stirringthe mixture was stirred for a few minutes
7. extractionthe water phase was extracted once with EtOAc
8. washthe combined EtOAc solutions was further washed with saturated NaHCO3 (aq) and brine
9. customThe crude material was purified by flash-chromatography on silica using a gradient of 0% to 40% EtOAc in Heptane
10. customfurther purified by HPLC

ORD-Eintrag

ord-c0df1a1f06594510850caa93589600ee

Quelldatensatz

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08030340B2