반응 #10652

반응 방정식

Intermediate 93

5-bromo-4-methylisoquinoline

Intermediate 93

5-bromo-4-methylisoquinoline

tri(tert-butyl)phosphine

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

sodium tert-butoxide

→

title compound

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

용매

ethyl acetate

toluene

반응 조건

후처리

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

실험 절차

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 (602 mg), tris(dibenzylideneacetone)dipalladium(0) (124 mg), tri(tert-butyl)phosphine (0.5 ml, Kanto Chemicals), cis-N-(tert-butoxycarbonyl)-1,4-cyclohexanediamine (697 mg) and sodium tert-butoxide (390 mg) in toluene was stirred with heating at 120° C. for 16.5 hours. The reaction mixture was cooled to room temperature and added with ethyl acetate (10 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 (45 mg).

출처