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

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Reaction Steps

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.

Provenance & Evidence