反応 #1784428

反応方程式

(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

溶媒

THF

反応条件

後処理

1. 1
   その他and then quenched with saturated ammonium chloride
2. 2
   workup.ADDITIONdiluted with ethyl acetate
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Purification by column chromatography (19:1 DCM/MeOH)

実験手順

(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).

出典