[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:19])/[C:11](=[CH:20]/[CH3:21])/[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[NH3:22].[BH4-].[Na+]>C1COCC1>[NH2:22][CH:20]([CH:11]1[CH2:10][C@@H:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]1[OH:19])[CH3:21]To a solution of (S,E)-4-(3,4-dichlorophenyl)-2-ethylidene-3,4-dihydronaphthalen-1(2H)-one (42) (0.60 g, 1.89 mmol) in THF (8 mL) at ambient temperature was added ammonia solution (2.0 M in MeOH, 2.83 mL, 5.67 mmol). The reaction mixture was stirred for 4 h before NaBH4 (0.14 g, 3.78 mmol) was added. The reaction mixture was stirred for 2 h before being quenched by a saturated solution of NH4Cl (8 mL). The product was extracted with diethyl ether (30 mL×2), dried and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane/0.1% DEA=1:7 to 1:5) to give (4S)-2-(1-aminoethyl)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-ol (43) (0.50 g, 50%).
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