Réaction #10587

Équation de réaction

Intermediate 1

N-(tert-butoxycarbonyl)-N′-[(5-isoquinolyl)sulfonyl]-1,3-propylenediamine

1,1′-azobis(N,N-dimethylformamide)

3-phenyl-1-propanol

tri(n-butyl)phosphine

→

title compound

N-(tert-butoxycarbonyl)-N′-[(5-isoquinolyl)sulfonyl]-N′-(3-phenylpropyl)-1,3-propylenediamine

3-phenyl-1-propanol

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGice cooling and stirred at room temperature under argon atmosphere for 13.5 hours
2. 2
   AutreThe precipitates in the reaction mixture
3. 3
   Autrewere removed by filtration
4. 4
   Autrethe solvent was evaporated from the filtrate under reduced pressure
5. 5
   AutreThe residue was purified by flash column chromatography (hexane/ethyl acetate mixed solvent)

Mode opératoire

A solution of Intermediate 1 (640 mg), 1,1′-azobis(N,N-dimethylformamide) (1200 mg, Aldrich or prepared according to Chemistry Letters, 539 (1994)) and 3-phenyl-1-propanol (710 μl, Tokyo Kasei Kogyo) in tetrahydrofuran (30 ml) was added with tri(n-butyl)phosphine (1.75 ml, Tokyo Kasei Kogyo) with stirring and ice cooling and stirred at room temperature under argon atmosphere for 13.5 hours. The precipitates in the reaction mixture were removed by filtration, and then the solvent was evaporated from the filtrate under reduced pressure. The residue was purified by flash column chromatography (hexane/ethyl acetate mixed solvent) to obtain the title compound (913 mg, mixture with a small amount of 3-phenyl-1-propanol).

Source