Réaction #6851

Équation de réaction

Sodium cyanoborohydride

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

sodium bicarbonate

→

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

Rendement 94.4%

Solvants

methanol

Conditions de réaction

Traitement

1. 1
   Autreto quench the excess hydride reagent
2. 2
   AutreThe methanol was evaporated under vacuum
3. 3
   workup.ADDITIONthe aqueous solution was diluted with sodium bicarbonate (saturated, 30 mL)
4. 4
   Extractionextracted with dichloromethane (2×30 mL)
5. 5
   SéchageThe combined organic layers were dried over sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Autreevaporated

Mode opératoire

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).

Source