[CH2:1]([N:8]1[C@H:17]([CH3:18])[CH2:16][C:15]2[C:10](=[C:11]([O:21]C)[CH:12]=[C:13]([O:19]C)[CH:14]=2)[C@H:9]1[CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-].[Na+].[BrH:26]>C(O)(=O)C>[BrH:26].[CH2:1]([N:8]1[C@H:17]([CH3:18])[CH2:16][C:15]2[C:10](=[C:11]([OH:21])[CH:12]=[C:13]([OH:19])[CH:14]=2)[C@H:9]1[CH3:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Into a 15 mL culture tube was placed N-benzyl-(1R, 3R)-1,2,3,4-tetrahydro-6,8-dimethoxy-1,3-dimethylisoquinoline (62 mg, 0.2 mmol) dissolved in acetic acid (1 mL). To this solution were added sodium iodide (120 mg, 0.8 mmol) and concentrated aqueous hydrobromic acid (49%, 2 mL). The mixture was heated at 100° C. for 3 hours and then cooled to 0° C., at which time light yellow crystals precipitated out of solution. Vacuum filtration with a glass fritted Buchner funnel gave the N-benzyl-(1R, 3R)-1,2,3,4-tetrahydro-6,8-dihydroxy-1,3-dimethyl-isoquinoline hydrobromide salt [105] (48 mg, 66%) as light yellow crystals.
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