Reaktion #10654

Reaktionsgleichung

Intermediate 93

5-bromo-4-methylisoquinoline

Intermediate 93

5-bromo-4-methylisoquinoline

tri(tert-butyl)phosphine

trans-N-(tert-butoxycarbonyl)-1,4-cyclohexanediamine

sodium tert-butoxide

→

title compound

trans-N-(tert-butoxycarbonyl)-N′-(4-methyl-5-isoquinolyl)-1,4-cyclohexanediamine

Lösungsmittel

ethyl acetate

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled to room temperature
2. 2
   Sonstigethe insoluble matters were removed by filtration through Celite
3. 3
   SonstigeThe solvent was evaporated under reduced pressure
4. 4
   Sonstigethe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Vorschrift

According to the method of Example 15, Step A, the title compound was synthesized from Intermediate 93. That is, under nitrogen atmosphere, a suspension of Intermediate 93 (1.13 g), tris(dibenzylideneacetone)dipalladium(0) (0.71 g), tri(tert-butyl)phosphine (0.5 ml), trans-N-(tert-butoxycarbonyl)-1,4-cyclohexanediamine (1.04 g) and sodium tert-butoxide (0.73 g) in toluene was stirred with heating at 120° C. for 1 hour. The reaction mixture was cooled to room temperature and added with ethyl acetate (50 ml), and the insoluble matters were removed by filtration through Celite. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to obtain the title compound (456 mg).

Quelle