[F:1][C:2]([F:14])([F:13])[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][N:4]=1.C(NC(=O)C(F)(F)F)CC1C=CC=CC=1.C(O)(C(F)(F)F)=O>O1CCCC1.[Ru]>[F:14][C:2]([F:1])([F:13])[CH:3]1[CH:12]2[CH:7]([CH2:8][CH2:9][CH2:10][CH2:11]2)[CH2:6][CH2:5][NH:4]120 g (0,101 mol) of 1-(Trifluoromethyl)-3,4-dihydroisoquinoline [prepared from N-(phenethyl)trifluoroacetamide analogously to U.S. Pat. No. 3,956,333 (11.5.76; Sterling Drug Inc.)] were hydrogenated in 100 ml of tetrahydrofuran on 5 g of ruthenium on alumina (about 10% Ru content) at 150° C. for 8 h at an H 2 pressure of 100 bar in a 0.3 1 V4A autoclave. After filtration, the THF was stripped off and the crude product was fractionareal in a water pump vacuum by means of a microdistillation apparatus. B.p.16 (main fraction): 94°-96° C. Yield: 19 g (0.092 mol) (91% of theory) The product was obtained as a diastereomer mixture. 19F--NMR: δ=+5.9 ppm(d, JH-F =8.5 Hz)(according to integral about 99%) 19F--NMR: δ=+14.2 ppm(d, JH-F =8.5 Hz) (according to integral <1%) (against external CF3COOH).
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