Sodium borohydride → 1,2,3,4-Tetrahydro-6-methoxy-1-phenylisoquinoline

HRID 397048Notes

Reaction equation

HRID 397048 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[N:10][CH2:9][CH2:8]2>CO>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH:10][CH2:9][CH2:8]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 10466684HCID 10466684, compound

Product 1

HCID 117763951,2,3,4-Tetrahydro-6-methoxy-1-phenylisoquinolineYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.945 g, 24.96 mmol) was added in small portions to a solution of 6-methoxy-1-phenyl-3,4-dihydroisoquinoline (1.480 g, 6.24 mmol) in MeOH (50 ml) at 0° C. The reaction mixture was stirred for 30 min, warmed to rt and stirred at rt for 19 hr, then quenched by the dropwise addition of H2O (10 ml). Excess MeOH was removed by evaporation and the resulting aqueous solution was extracted with CHCl3 (4×10 ml). The combined organic extracts were dried over MgSO4 and concentrated in vacuo to give 1.308 g (88% yield) of white solid.

Workup

  1. stirringstirred at rt for 19 hr
  2. customquenched by the dropwise addition of H2O (10 ml)
  3. customExcess MeOH was removed by evaporation
  4. extractionthe resulting aqueous solution was extracted with CHCl3 (4×10 ml)
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7f3685e041e2493790a908d6ea2ee5da
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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