Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[NH2:7][CH2:8][CH:9]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[C:15]([F:20])[CH:14]=1)[CH2:10][CH2:11][OH:12].C(N(CC)CC)C>C(Cl)Cl>[F:20][C:15]1[CH:14]=[C:13]([CH:9]([CH2:8][NH:7][C:2]([O:4][CH2:5][CH3:6])=[O:3])[CH2:10][CH2:11][OH:12])[CH:18]=[CH:17][C:16]=1[F:19]Ethyl chloroformate (3.9 mL, 40.8 mmol) was added dropwise to a stirred cooled (−40° C.) solution of 4-amino-3-(3,4-difluorophenyl)-1-butanol (7.45 g, 37 mmol) and triethylamine (5.94 mL, 42.6 mmol) in DCM (180 mL). The solution was stirred at room temperature for 30 min and at room temperature overnight. The material was washed twice with 1N HCl, twice with saturated sodium bicarbonate; dried (Na2SO4), filtered and the solvent removed to provide the title compound (8.85 g, 88%) as a yellow oil. 1H-NMR (CDCl3) δ 1.18-1.23 (t, 3H, CH) 1.72-1.98 (m, 3H) 2.96-3.00 (m, 1H, CH) 3.24-3.29 (m, 1H, CH) 3.45-4.04 (m, 3H, CH), 4.06-4.14 (m, 2H, CH) 4.66 (br. s, 1H, OH or NH) 6.91-7.37 (m, 3H, ArH). MS m/z 274 (M+H).
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