[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].[CH3:22][NH2:23].[BH4-].[Na+]>C1COCC1>[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)[CH:12]([OH:19])[CH:11]([CH:20]([NH:23][CH3:22])[CH3:21])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]To a solution of 42 (0.80 g, 2.52 mmol) in THF (10 mL) at ambient temperature was added methylamine solution (2.0 M in THF, 3.78 mL, 7.56 mmol). The reaction mixture was stirred for 4 h before NaBH4 (0.44 g, 11.49) was added. The reaction mixture was stirred for 3 h before being quenched by a saturated solution of NH4Cl (10 mL). The product was extracted with diethyl ether, 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)-4-(3,4-dichlorophenyl)-2-(1-(methylamino)ethyl)-1,2,3,4-tetrahydronaphthalen-1-ol (44) (493 mg, 56%).
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