Sodium Hydroxide → HCID 131719404, compound

Participants

Reaction Steps

Sodium borohydride (0.465 G) was added portionwise to a mixture of 1-[1-(2-cyanophenyl)cyclobutyl]-6,7-dimethoxy-2-methyl-3,4-dihydroisoquinolinium iodide (6 g) and methanol (40 ml). The mixture was stirred for 2 hours then poured onto aqueous sodium hydroxide solution and the product extracted into ether. The solvent was removed from the extracts to give a gum which was dissolved in ethyl acetate and a little propan-2-ol. A 0.4M solution of (±)-dibenzoyltartaric acid in ether (35 ml) was added and the resulting suspension was concentrated in vacuo. The residual solid was washed with ether to give 1-[1-(2-cyanophenyl)cyclobutyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (±)-dibenzoyltartrate (7.2 g), m.p. 109°-112° C. (dec).

Provenance & Evidence