반응 #1784428

반응 방정식

(4S,5S)-Tert-butyl 5-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyl-4-((2-methylpyridin-4-yl)methyl)oxazolidine-3-carboxylate

TBAF

→

title compound

(4S,5S)-tert-butyl 5-(hydroxymethyl)-2,2-dimethyl-4-((2-methylpyridin-4-yl)methyl)oxazolidine-3-carboxylate

용매

THF

반응 조건

후처리

1. 1
   기타and then quenched with saturated ammonium chloride
2. 2
   workup.ADDITIONdiluted with ethyl acetate
3. 3
   기타The layers were separated
4. 4
   추출the aqueous layer was extracted with EtOAc
5. 5
   세척The combined organic layers were washed with water, brine
6. 6
   건조dried over sodium sulfate
7. 7
   농축concentrated
8. 8
   기타Purification by column chromatography (19:1 DCM/MeOH)

실험 절차

(4S,5S)-Tert-butyl 5-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyl-4-((2-methylpyridin-4-yl)methyl)oxazolidine-3-carboxylate (0.083 g, 0.18 mmol) was dissolved in THF (2 mL) and cooled to 0° C. Next, TBAF (0.28 ml, 0.28 mmol) was added dropwise and the reaction was stirred 1 hr. and then quenched with saturated ammonium chloride and diluted with ethyl acetate. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with water, brine, dried over sodium sulfate, and concentrated. Purification by column chromatography (19:1 DCM/MeOH) afforded the title compound, MS m/z: 337.2 (100%, M+1).

출처