Reacción #69133

Ecuación de reacción

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

n-BuLi

1-Methyl-4-piperidone

→

title compound

Rendimiento 85.0%

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

Rendimiento 85.0%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente