반응 #41430

반응 방정식

(S)-tert-butyl 1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate

isopropylmagnesium chloride

HCl

3-bromoquinoline

→

subtitle compound

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

용매

THF

THF

EtOAc

THF Hexane

반응 조건

후처리

1. 1
   기타a solution was formed
2. 2
   workup.STIRRINGThe mixture was stirred at −10° C. for 30 min
3. 3
   기타to reach r.t.
4. 4
   workup.STIRRINGstirred over night, 15 h
5. 5
   workup.ADDITIONThe reaction mixture, a clear red solution, was slowly poured into ice-
6. 6
   workup.STIRRINGthe mixture was stirred for a few min
7. 7
   추출the water phase was extracted once with EtOAc
8. 8
   세척the combined EtOAc solutions was further washed with saturated NaHCO3 (aq) and brine
9. 9
   기타The crude material was purified by flash-chromatography on silica using a gradient of 0% to 40% EtOAc in Heptane
10. 10
    기타further purified by HPLC

실험 절차

(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%)

출처