반응 #86227

반응 방정식

2,6-dibromopyridine

n-BuLi

hexane

tert-butyl 4-oxoazepane-1-carboxylate

→

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

수율 64.1%

용매

H2O

Et2O

Et2O

반응 조건

후처리

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

실험 절차

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]+.

출처