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A cooled (0° C.) solution of (rac)-4-(8-hydroxy-5,6,7,8-tetrahydroisoquinolin-4-yl)benzonitrile (example 11) (50 mg, 200 μmol) in DMF (1.4 mL) was treated with NaH (55% in oil, 9.6 mg, 220 μmol) and after ½ h with methyl iodide (13.7 μL, 220 μmol) in DMF (0.2 mL). After stirring 1 h at 0° C. and 1.5 h at room temperature, the reaction mixture was poured on aq. sat. NaHCO3 solution followed by extraction with AcOEt (3×). The organic phases were washed once with aq. sat. NaCl solution. The combined organic phases were dried (Na2SO4), filtered and purified by flash chromatography (50 g SiO2, Telos-cartridge, CH2Cl2/MeOH 1%). Precipitation from CH2Cl2 with n-pentane gave the title compound (17 mg, 32%) as off-white powder. MS: 265.1 (M+H+).

1. extractionfollowed by extraction with AcOEt (3×)
2. washThe organic phases were washed once with aq. sat. NaCl solution
3. dry with materialThe combined organic phases were dried (Na2SO4)
4. filtrationfiltered
5. custompurified by flash chromatography (50 g SiO2, Telos-cartridge, CH2Cl2/MeOH 1%)
6. customPrecipitation from CH2Cl2 with n-pentane