Formaldehyde → HCID 12303970, compound

Participants

Reaction Steps

6,7-Dimethoxy-1-(4-methoxybenzyl)-1,2,3,4-tetrahydroisoquinolin-8-ol (2.55 g, 7.74 mmol) obtained in Example 1-2 was dissolved in 100 ml of chloroform-methanol (1:1), 35% formalin (3.6 ml, 45.3 mmol) was added and the mixture was stirred at room temperature for 2 hours. Sodium borohydride (3.40 g, 89.8 mmol) was added under ice cooling and the mixture was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure, 200 ml of water was added to the resultantresidue, and the mixture was neutralized with 1N hydrochloric acid and thenextracted with chloroform (100 ml×3). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol) to give 2.09 g (yield: 79%) of the captioned compound as pale yellow powder. Melting point: 112°-114° C. FAB-MS (m/z, (C20H25NO4 +H)+ ): 344 1H-NMR (300MHz, CDCl3, δ ppm): 2.35 (3H, s), 2.35-2.45 (1H, m), 2.73-2.87 (2H, m), 2.98 (1H, dd, J=3.2Hz, 14.2Hz), 3.20-3.32 (1H, m), 3.78(3H, s), 3.83 (3H, s), 3.88 (3H, s), 3.95 (1H, d, J=3.2Hz, 8.8Hz), 6.20 (1H, s), 6.80 (1H, d, J=8.8Hz), 7.18 (1H, d, J=8.8Hz)

Provenance & Evidence