Reacción #6851

Ecuación de reacción

Sodium cyanoborohydride

7-methoxy-1-methyl-3,4-dihydro-isoquinoline

sodium bicarbonate

→

7-methoxy-1-methyl-1,2,3,4-tetrahydro-isoquinoline

Rendimiento 94.4%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto quench the excess hydride reagent
2. 2
   OtroThe methanol was evaporated under vacuum
3. 3
   workup.ADDITIONthe aqueous solution was diluted with sodium bicarbonate (saturated, 30 mL)
4. 4
   Extracciónextracted with dichloromethane (2×30 mL)
5. 5
   SecadoThe combined organic layers were dried over sodium sulfate
6. 6
   Filtraciónfiltered
7. 7
   Otroevaporated

Procedimiento

Sodium cyanoborohydride (0.43 g) was added to a solution of 7-methoxy-1-methyl-3,4-dihydro-isoquinoline (2.67 g) in methanol (41 mL). The mixture was stirred at rt for 20 min. Aqueous sodium bicarbonate (saturated, 10 mL) was added to quench the excess hydride reagent. The methanol was evaporated under vacuum and the aqueous solution was diluted with sodium bicarbonate (saturated, 30 mL) and extracted with dichloromethane (2×30 mL). The combined organic layers were dried over sodium sulfate, filtered and evaporated to afford 7-methoxy-1-methyl-1,2,3,4-tetrahydro-isoquinoline (2.55 g).

Fuente