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

Temperature

-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 min and was the allowed to reach r.t. 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 min, 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 min
3. customto reach r.t.
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 min
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 record

ord-e8677d9cda1d48b590ebce478e9d99c8

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07728030B2