反应 #86227

反应方程式

2,6-dibromopyridine

n-BuLi

hexane

tert-butyl 4-oxoazepane-1-carboxylate

→

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

收率 64.1%

溶剂

H2O

Et2O

Et2O

反应条件

后处理

1. 1
   workup.STIRRINGAfter the mixture was stirred for one hour, to it
2. 2
   萃取The aqueous layer was extracted with EtOAc (100 mL×2)
3. 3
   洗涤The combined organic layers were washed with 10% solution of NaOH and brine
4. 4
   干燥dried over MgSO4
5. 5
   浓缩concentrated under reduced pressure
6. 6
   其他The crude product was purified by silica gel chromatography
7. 7
   洗涤as eluting solvents

实验过程

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]+.

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