[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([NH:12][CH2:13][C@H:14]([OH:21])[C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=O)=[CH:4][CH:3]=1.[B].CSC.CO.Cl>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][NH:12][CH2:13][C@@H:14]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[OH:21])=[CH:6][CH:7]=1
To a suspension of 3-(4-bromophenyl)-N-[(2R)-2-hydroxy-2-(3-pyridyl)ethyl]propanamide (3.42 g) in tetrahydrofuran (58 ml) was added 2.0M dimethyl sulfide—borane (1:1) in tetrahydrofuran (16.1 ml) dropwise at 0-5° C. over 45 minutes. After cooling to room temperature, to the reaction mixture were added methanol (2.99 ml) and 37% hydrochloric acid (4.8 ml) at 4° C. (ice bath). The mixture was stirred at 80° C. for 1 hour. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure and to the residue was added water (100 ml). The pH was adjusted to 10 with 24% aqueous sodium hydroxide solution at 4° C. and the mixture was extracted with ethyl acetate (200 ml). The organic layer was washed with water and brine and dried over magnesium sulfate. Filtration followed by evaporation under reduced pressure gave (1R)-2-[[3-(4-bromophenyl)propyl]-amino]-1-(3-pyridyl)ethanol (3.22 g) as a yellow oil.
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