Réaction #166361

Équation de réaction

K2CO3

2-(piperidin-4-yl)ethanol

t-butylchlorodimethylsilane

K2CO3

imidazole

→

compound 292

Rendement 86.0%

4-(2-(t-Butyldimethylsilyloxy)ethyl)piperidine

Rendement 86.0%

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   Extractionextracted with dichloromethane (3×30 mL)
2. 2
   SéchageThe combined organics were dried (MgSO4)
3. 3
   Autreevaporated
4. 4
   Autreto give a pale yellow oil
5. 5
   LavageSilica gel chromatography (gradient elution dichloromethane+2.5% TEA/0-10% methanol)
6. 6
   Autreafforded a white solid
7. 7
   Extractionextracted with dichloromethane+10% methanol (3×30 mL)
8. 8
   Séchagethe organics dried (MgSO4)
9. 9
   Autreevaporated

Mode opératoire

2-(piperidin-4-yl)ethanol (2.00 g, 15.5 mmol), t-butylchlorodimethylsilane (2.57 g, 17.0 mmol), and imidazole (1.05 g, 15.5 mmol) were taken up in dichloromethane (15 mL) and stirred for 22 hours. This solution was added to aqueous K2CO3 (80 mL) and extracted with dichloromethane (3×30 mL). The combined organics were dried (MgSO4) and evaporated to give a pale yellow oil. Silica gel chromatography (gradient elution dichloromethane+2.5% TEA/0-10% methanol) afforded a white solid. This solid was added to aqueous K2CO3 (60 mL) and extracted with dichloromethane+10% methanol (3×30 mL), the organics dried (MgSO4) and evaporated to give compound 292 as a yellow oil (3.24 g, 86%).

Source