반응 #974539

반응 방정식

2-bromo-5-(2-methyl-1,3-dioxolan-2-yl)pyridine

n-BuLi

1-Methyl-4-piperidone

→

title compound

수율 85.0%

1-methyl-4-(5-(2-methyl-1,3-dioxolan-2-yl)pyridin-2-yl)piperidin-4-ol

수율 85.0%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.STIRRINGto stir at −78° C. for 20 minutes
2. 2
   온도then warmed slowly to ambient temperature
3. 3
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 18 hours
4. 4
   농축concentrated in vacuo
5. 5
   기타The residue was purified on silica gel by flash column chromatography

실험 절차

2-bromo-5-(2-methyl-1,3-dioxolan-2-yl)pyridine (500 mg, 2.048 mmol) (described in the literature: Bioorg. Med. Chem., 2005, 13, 6763) was dissolved in anhydrous tetrahydrofuran (10 mL) and cooled to −78° C. under nitrogen. n-BuLi (901.2 μL of 2.5 M, 2.253 mmol) was added dropwise and the reaction mixture was stirred at −78° C. for 30 minutes. 1-Methyl-4-piperidone (602.6 mg, 655.0 μL, 5.325 mmol) was added and the reaction was allowed to stir at −78° C. for 20 minutes then warmed slowly to ambient temperature. The reaction mixture was stirred at room temperature for 18 hours and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography to afford the title compound as a sticky orange solid (483.4 mg, 85% yield).

출처