반응 #1784430

반응 방정식

MeI

N-BUTYLLITHIUM

Dimethylethanolamine

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

→

titled compound

(4S,5S)-tert-butyl 5-((tert-butyldimethylsilyloxy)methyl)-4-((2-chloro-6-methylpyridin-4-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate

용매

THF

—

hexanes

—

hexanes

반응 조건

후처리

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.STIRRINGthe solution was stirred for 1 hour at −78° C.
3. 3
   기타to give a dark orange solution
4. 4
   온도to slowly warm to 0° C.
5. 5
   기타was quenched with saturated aqueous ammonium chloride
6. 6
   workup.ADDITIONThe reaction was diluted with ethyl acetate and water
7. 7
   기타separated
8. 8
   추출The aqueous layer was extracted with ethyl acetate
9. 9
   세척the combined organic layers were washed with water, brine
10. 10
    건조dried over sodium sulfate
11. 11
    농축concentrated

실험 절차

Dimethylethanolamine (0.128 ml, 1.27 mmol) was added to anhydrous hexanes (1.4 L) and cooled to 0° C. N-BUTYLLITHIUM (2.5 M in hexanes)(1.02 ml, 2.55 mmol) was added dropwise and stirred for 30 minutes before being cooled to −78° C. (4S,5S)-Tert-butyl 5-((tert-butyldimethylsilyloxy)methyl)-4-((2-chloropyridin-4-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate (0.200 g, 0.425 mmol) in hexanes (1 mL) was added dropwise and the solution was stirred for 1 hour at −78° C. to give a dark orange solution. MeI (0.106 ml, 1.70 mmol) in THF (3.2 mL) was added dropwise and the reaction was allowed to slowly warm to 0° C. and was quenched with saturated aqueous ammonium chloride. The reaction was diluted with ethyl acetate and water and separated. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with water, brine, dried over sodium sulfate, and concentrated to give the titled compound which was used directly for the next step without purification.

출처