[CH2:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([OH:16])=[C:9]([O:14][CH3:15])[CH:10]=2)[CH:5]1[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=1)[CH:2]=[CH2:3].FC(F)(F)C(O)=O>O=[V].Cl.Cl.Cl.C(Cl)Cl>[CH2:1]([N:4]1[CH:5]2[C:6]3=[C:7]([C:8]([OH:16])=[C:9]([O:14][CH3:15])[CH:10]=[C:11]3[CH2:12][CH2:13]1)[C:23]1[CH:22]=[C:21]([O:24][CH3:25])[C:20]([O:26][CH3:27])=[CH:19][C:18]=1[CH2:17]2)[CH:2]=[CH2:3]22 g. (59.54 mmol) (+)-2-Allyl-7-hydroxy-6-methoxy-1-(3,4-dimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline in a mixture of 190 ml. trifluoroacetic acid and 190 ml. anhydrous methylene chloride are mixed at -10° C., with the exclusion of moisture, with a solution of 6.0 ml. (11.04 g., 63.7 mmol) vanadium oxytrichloride in 190 ml. anhydrous methylene chloride. The reaction mixture is stirred for 30 minutes at -10° C., for 1 hour at 0° C. and for 2 hours at ambient temperature. Thereafter, the reaction mixture is concentrated to about one third of its volume by evaporation of the solvent in a vacuum at ambient temperature. The residue is mixed with ice water and extracted with chloroform. The chloroform phase is rendered basic with an aqueous solution of ammonia and worked up in the usual manner. By crystallisation from ethanol, there is obtained (+)-6-allyl-5,6,6a,7-tetrahydro-1-hydroxy-2,9,10-trimethoxy-4H-dibenzo(de,g)quinoline; m.p. 85°-93° C./134°-138° C.
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