Reaktion #86227

Reaktionsgleichung

2,6-dibromopyridine

n-BuLi

hexane

tert-butyl 4-oxoazepane-1-carboxylate

→

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

Ausbeute 64.1%

Lösungsmittel

H2O

Et2O

Et2O

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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]+.

Quelle