반응 #48299

반응 방정식

1-Iodopropane

(4S,5S)-Tert-butyl 4-((2-(tert-butyldimethylsilyl)thiazol-4-yl)methyl)-5-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate

N-BUTYLLITHIUM

→

title compound

(4S,5S)-tert-butyl 4-((2-(tert-butyldimethylsilyl)-5-propylthiazol-4-yl)methyl)-5-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate

용매

THF

반응 조건

후처리

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   온도cooled to −78° C
3. 3
   온도to slowly warm to −50° C.
4. 4
   기타The reaction was quenched with saturated ammonium chloride
5. 5
   기타The layers were separated
6. 6
   추출the aqueous layer was extracted with ethyl acetate
7. 7
   세척The combined organic layers were washed with water, brine
8. 8
   건조dried over sodium sulfate

실험 절차

(4S,5S)-Tert-butyl 4-((2-(tert-butyldimethylsilyl)thiazol-4-yl)methyl)-5-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate (0.150 g, 0.269 mmol) in THF (3 mL) was cooled to −78° C. when N-BUTYLLITHIUM (2.5 M in hexanes) (0.1 19 ml, 0.296 mmol) was added dropwise. The solution was warmed to −50° C. for 40 minutes and then cooled to −78° C. 1-Iodopropane (0.0549 g, 0.323 mmol) was added dropwise and the solution was allowed to slowly warm to −50° C. and stirred for 1 hr. The reaction was quenched with saturated ammonium chloride. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water, brine and dried over sodium sulfate to afford the title compound, which was used without further purification for the next step.

출처