Réaction #86227

Équation de réaction

2,6-dibromopyridine

n-BuLi

hexane

tert-butyl 4-oxoazepane-1-carboxylate

→

tert-butyl 4-(6-bromopyridin-2-yl)-4-hydroxyazepane-1-carboxylate

Rendement 64.1%

Solvants

H2O

Et2O

Et2O

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGAfter the mixture was stirred for one hour, to it
2. 2
   ExtractionThe aqueous layer was extracted with EtOAc (100 mL×2)
3. 3
   LavageThe combined organic layers were washed with 10% solution of NaOH and brine
4. 4
   Séchagedried over MgSO4
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   AutreThe crude product was purified by silica gel chromatography
7. 7
   Lavageas eluting solvents

Mode opératoire

To a solution of 2,6-dibromopyridine (0.2 g, 0.84 mmol) in Et2O (20 mL) at −78° C. was added 2.5 M solution of n-BuLi in hexane (3.7 mL, 0.928 mmol) over 30 min. The mixture was stirred at −78° C. for 30 minutes. To it was dropped tert-butyl 4-oxoazepane-1-carboxylate (180 mg, 084 mmol) in Et2O (20 mL) over 15 minutes. After the mixture was stirred for one hour, to it was added H2O (100 mL). The aqueous layer was extracted with EtOAc (100 mL×2). The combined organic layers were washed with 10% solution of NaOH and brine, dried over MgSO4, concentrated under reduced pressure. The crude product was purified by silica gel chromatography using petroleum ether/EtOAc (9:1) as eluting solvents to afford tert-butyl 4-(6-bromopyridin-2-yl)-4-hydroxyazepane-1-carboxylate as an oil (200 mg, 62.5%). MS (ESI) m/z: 371 [M+H]+.

Source