تفاعل #69133

معادلة التفاعل

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

n-BuLi

1-Methyl-4-piperidone

→

title compound

المردود 85.0%

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

المردود 85.0%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر