[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([SH:14])=[CH:9][CH:10]=2)[CH2:5]1)(=[O:3])[CH3:2].[CH3:15][O-].[Na+].IC>CO>[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([S:14][CH3:15])=[CH:9][CH:10]=2)[CH2:5]1)(=[O:3])[CH3:2]A suspension of N-acetyl-7-mercapto-1,2,3,4-tetrahydroisoquinoline (1.0 gm., 0.0048 m.) in 20 ml. of methanol was stirred in a nitrogen atmosphere. Sodium methoxide (0.3 gm., 0.0055 m.) and 5 ml. of iodomethane were added to the suspension. The mixture was stirred at 25° C. for thirty minutes, evaporated and partitioned between chloroform and water. The chloroform layer was washed, dried over sodium sulfate and evaporated. The residue was chromatographed on silica gel, eluted with ethyl acetate to give pure N-acetyl-7-methylthio-1,2,3,4-tetrahydroisoquinoline.
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