Reaktion #69133

Reaktionsgleichung

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

n-BuLi

1-Methyl-4-piperidone

→

title compound

Ausbeute 85.0%

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

Ausbeute 85.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle