Sodium Carbonate → HCID 68685692, compound

Participants

Reaction Steps

1-biphenyl-3-ylmethyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline oxalate (43) was prepared as follows: 1-(3-bromo-benzyl)-6,7-dimethoxy -1,2,3,4-tetrahydro-isoquinoline oxalate (0.910 g, 2.01 mmol) was added to a mixture of 50 mL CH2Cl2 and 50 ml of 1N NaOH. The reaction mixture was stirred at room temperature. After dissolving of precipitate organic phase was separated, dried over Na2SO4, filtered and evaporated. A residue was dissolved in 10 mL i-PrOH. Phenyl-boronic acid (0.268 g, 2.2 mmol) was added. The resulting solution was stirred for 30 min at room temperature. Pd(OAc)2 (2 mg, 0.0089 mmol), PPh3 (11 mg, 0.042 mmol) and 2N Na2CO3 (1.3 mL, 2.6 mmol) were added, the reaction mixture was refluxed for 6 h under Ar and evaporated. A residue was dissolved in chloroform and washed with 1N NaOH. Organic phase was dried under Na2SO4, filtered and evaporated. A residue was dissolved in MeOH, a solution of oxalic acid dihydrate (0.510 g, 4.05 mmol) was added under reflux. Oxalic acid salt was crystallized from MeOH—Et2O mixture. Yield is 0.558 g (61.7%)

Provenance & Evidence