Sodium borohydride → 1-[2-(4-Chlorophenyl)ethyl]-6-methyl-7-methoxy-1,2,3,4-tetrahydroisoquinoline

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Reaction Steps

Add sodium borohydride (2.0 g) to a suspension of the dihydroisoquinoline from step B (4.75 g) in ethanol (175 mL) and stir the mixture for 2 h. Concentrate to a residue, treat with water and heat on a steam bath for 0.75 h. Cool the mixture to room temperature, extract with ether and concentrate the ethereal extract to a residue. Dissolve the residue in ethyl acetate, treat with 1.7 g of maleic acid and recrystallize the resulting salt from ethanol/ethyl acetate to give the title compound as the maleate salt (4.05 g). Elemental analysis: calc. for C19H22ClNO2, C=63.9%, H=6.03%, N=3.25%; found, C=63.91, H=5.99, N=3.22.

Provenance & Evidence