Реакция #73470

Уравнение реакции

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

Выход 9.5%

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

Выход 9.5%

Растворители

dimethylacetamide

Условия реакции

Обработка

1. 1
   Экстракцияthe mixture extracted three times
2. 2
   ДругоеThe organic layer was dried
3. 3
   Другоеevaporated
4. 4
   ДругоеThe residue was purified
5. 5
   ДругоеThe 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
   Экстракцияthe mixture extracted three times
8. 8
   ДругоеThe organic layer was dried
9. 9
   Фильтрацияfiltered
10. 10
    Другоеevaporated

Методика

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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