반응 #1460251

반응 방정식

sodium borohydride

sodium hydrogencarbonate

5-amino-1-chloro-4-vinylisoquinoline

Intermediate 9

tert-Butyl N-benzyl-(4-oxo-cyclohexyl)carbamate

→

title compound

수율 61.7%

tert-Butyl trans-N-benzyl-[4-(1-chloro-4-vinylisoquinolin-5-yl)aminocyclohexyl]carbamate

수율 61.7%

용매

methanol

ethyl acetate

dichloromethane

반응 조건

후처리

1. 1
   workup.STIRRINGstirred at room temperature for two hours
2. 2
   기타the precipitates were removed by filtration
3. 3
   기타Then, the organic layer was separated
4. 4
   기타the solvent was evaporated under reduced pressure
5. 5
   기타The residue was purified by silica gel column chromatography (n-hexane:acetone=5:4)

실험 절차

A solution of 5-amino-1-chloro-4-vinylisoquinoline (0.6 g) and Intermediate 9 (1.8 g) in dichloromethane (13 ml) was added with titanium tetraisopropoxide (1.7 ml) at room temperature, and stirred at room temperature for 22 hours. The reaction mixture was added with methanol (13 ml), and sodium borohydride (444 mg), and stirred at room temperature for two hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate (60 ml), and ethyl acetate (60 ml), and the precipitates were removed by filtration. Then, the organic layer was separated, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:acetone=5:4) to obtain the title compound (890 mg).

출처