反応 #1126901

反応方程式

(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

溶媒

THF

反応条件

後処理

1. 1
   その他quenched with saturated ammonium chloride
2. 2
   workup.ADDITIONdiluted with EtOAc
3. 3
   その他The layers were separated
4. 4
   抽出the aqueous layer was extracted with EtOAc
5. 5
   洗浄The combined organic layers were washed with water, brine
6. 6
   乾燥dried over sodium sulfate
7. 7
   濃縮concentrated
8. 8
   その他The crude material was purified by silica column chromatography (19:1 DCM/MeOH)

実験手順

(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).

出典