Reaction #10597

Reaction equation

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

Solvents

tetrahydrofuran

Conditions

Workup

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

Procedure

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.

Source