[H-].[Al+3].[Li+].[H-].[H-].[H-].CO[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([O:21][Si](C)(C)C)([C:19]#[N:20])[CH2:14][CH2:13][CH2:12]2.[F-].[Na+].O.[O:29]1CCC[CH2:30]1>>[NH2:20][CH2:19][C:15]1([OH:21])[C:16]2[C:11](=[C:10]([O:29][CH3:30])[CH:9]=[CH:18][CH:17]=2)[CH2:12][CH2:13][CH2:14]1Under nitrogen, to the slurry of lithium aluminum hydride (11.4 g) in tetrahydrofuran (200 ml) was added 6-methoxy-1-(trimethylsilanyloxy)-1,2,3,4-tetrahydronaphthalene-1-carbonitrile (41.3 g) in tetrahydrofuran (200 ml) dropwise at 5° C., and the mixture was stirred at the same temperature for 1 hour and at room temperature for 2 hours. To the mixture were added sodium fluoride (12.6 g) and water (16.2 ml) at 5° C., and the mixture was vigorously stirred at room temperature for 30 minutes. The precipitate was removed by filtration and the filter cake was washed with ethyl acetate-ethanol (95:5). The filtrate was evaporated in vacuo to afford 1-aminomethyl-5-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol (28.6 g).
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