تفاعل #48299

معادلة التفاعل

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

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   درجة الحرارةcooled to −78° C
3. 3
   درجة الحرارةto slowly warm to −50° C.
4. 4
   أخرىThe reaction was quenched with saturated ammonium chloride
5. 5
   أخرىThe layers were separated
6. 6
   استخلاصthe aqueous layer was extracted with ethyl acetate
7. 7
   غسيلThe combined organic layers were washed with water, brine
8. 8
   تجفيفdried over sodium sulfate

الإجراء التجريبي

(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.

المصدر