Réaction #69133

Équation de réaction

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

n-BuLi

1-Methyl-4-piperidone

→

title compound

Rendement 85.0%

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

Rendement 85.0%

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source