반응 #48305

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

TBAF

→

title compound

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

용매

THF

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후처리

1. 1
   기타quenched with saturated ammonium chloride
2. 2
   workup.ADDITIONdiluted with EtOAc
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
   기타The crude material was purified by silica column chromatography (19:1 DCM/MeOH)

실험 절차

(4S,5S)-Tert-butyl 5-((tert-butyldimethylsilyloxy)methyl)-4-((2-chloro-6-methylpyridin-4-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate (0.206 g, 0.425 mmol) was dissolved in THF (4 mL) and cooled to 0° C. TBAF (0.637 ml, 0.637 mmol) was added to the mixture dropwise and the reaction was stirred 1 hr and then quenched with saturated ammonium chloride and diluted with EtOAc. 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. The crude material was purified by silica column chromatography (19:1 DCM/MeOH) and then reverse phase HPLC to give the title compound. MS m/z: 371.3 (100%, M+1).

출처