Sodium Bicarbonate → 7-Methoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline

HRID 6755Notes

Reaction equation

HRID 6755 reaction equation
C([BH3-])#N.[Na+].[CH3:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][N:13]=[C:14]2[CH3:17])=[CH:9][CH:8]=1.C(=O)(O)[O-].[Na+]>CO>[CH3:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][NH:13][CH:14]2[CH3:17])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 150619777-Methoxy-1-methyl-3,4-dihydroisoquinoline

Product 1

HCID 159400117-Methoxy-1-methyl-1,2,3,4-tetrahydroisoquinolineYield 94.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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).

Workup

  1. customto quench the excess hydride reagent
  2. customThe methanol was evaporated under vacuum
  3. additionthe aqueous solution was diluted with sodium bicarbonate (saturated, 30 mL)
  4. extractionextracted with dichloromethane (2×30 mL)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-ac6e3f79f8e84358b70ca30390b52cd6
Source dataset
uspto-grants-2006_08
Patent number
US07084154B2

Reaction notes

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