반응 #73470

반응 방정식

NaHCO3

NaH

(1S,4S,5S)-5-(1-Amino-propyl)-5-phenyl-bicyclo[2.2.1]heptan-2-ol

7-chloro-6-fluoro-1-methoxy-isoquinoline

7-Chloro-6-fluoro-1-methoxy-isoquinoline

→

desired product 90

수율 9.5%

1-[(1S,2S,4S)-5-(7-Chloro-1-methoxy-isoquinolin-6-yloxy)-2-phenyl-bicyclo[2.2.1]hept-2-yl]-propylamine

수율 9.5%

용매

dimethylacetamide

반응 조건

후처리

1. 1
   추출the mixture extracted three times
2. 2
   기타The organic layer was dried
3. 3
   기타evaporated
4. 4
   기타The residue was purified
5. 5
   기타The product-containing fractions were evaporated to half of the original volume, 10 mL of a saturated aqueous Na2CO3-solution
6. 6
   workup.ADDITIONwas added
7. 7
   추출the mixture extracted three times
8. 8
   기타The organic layer was dried
9. 9
   여과filtered
10. 10
    기타evaporated

실험 절차

200 mg (0.82 mmol) of (1S,4S,5S)-5-(1-Amino-propyl)-5-phenyl-bicyclo[2.2.1]heptan-2-ol (89) were dissolved in 5 mL anhydrous dimethylacetamide. Afterwards, 39 mg (1.63 mmol) of NaH were added, followed by the addition of 173 mg (0.82 mmol) of 7-chloro-6-fluoro-1-methoxy-isoquinoline (10). The mixture was stirred at ambient temperature for 20 h. Afterwards, 50 mL of a saturated aqueous NaHCO3-solution were added and the mixture extracted three times using 30 mL ethyl acetate each. The organic layer was dried using MgSO4 and evaporated. The residue was purified using chromatography on reversed phase (acetonitrile/water). The product-containing fractions were evaporated to half of the original volume, 10 mL of a saturated aqueous Na2CO3-solution was added and the mixture extracted three times using 20 mL of ethyl acetate each. The organic layer was dried using MgSO4, filtered and evaporated yielding 34 mg of the desired product 90. Rt=0.86 min (Method 18). Detected mass: 437.3 (M+H+)

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