反应 #10597

反应方程式

tri(n-butyl)phosphine

1-chloro-5-hydroxyisoquinoline

(3-hydroxypropyl)carbamic acid tert-butyl ester

1,1′-azobis(N,N-dimethylformamide)

→

title compound

N-(tert-butoxycarbonyl)-3-[(1-chloro-5-isoquinolyl)oxy]propylamine

溶剂

tetrahydrofuran

反应条件

后处理

1. 1
   其他synthesized
2. 2
   其他The deposited solid was removed by filtration
3. 3
   其他the solvent was evaporated under reduced pressure
4. 4
   其他Then, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

实验过程

A suspension of 1-chloro-5-hydroxyisoquinoline (539 mg, synthesized according to the method described in a reference (Georgian, V. et al., J. Org. Chem., 27, 4571 (1962))), (3-hydroxypropyl)carbamic acid tert-butyl ester (1.58 g, Tokyo Kasei Kogyo) and 1,1′-azobis(N,N-dimethylformamide) (1.55 g) in tetrahydrofuran (8 ml) was added with tri(n-butyl)phosphine (2.24 ml) with ice cooling and stirred at room temperature for 24 hours. The deposited solid was removed by filtration, and the solvent was evaporated under reduced pressure. Then, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1) to obtain the title compound (860 mg) as white powdery solid.

来源