[F:1][C:2]([F:13])([F:12])[CH2:3][O:4][C:5]1[N:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1.C([O:16][C:17]([C:19]1([CH2:26][CH2:27]OC)[CH2:24][CH2:23][CH:22]([OH:25])[CH2:21][CH2:20]1)=O)C.[Cl-].C[Al+]C>C1(C)C=CC=CC=1>[OH:25][CH:22]1[CH2:23][CH2:24][C:19]2([C:17](=[O:16])[N:11]([C:8]3[CH:9]=[N:10][C:5]([O:4][CH2:3][C:2]([F:1])([F:12])[F:13])=[CH:6][CH:7]=3)[CH2:27][CH2:26]2)[CH2:20][CH2:21]16-(2,2,2-Trifluoro-ethoxy)-pyridin-3-ylamine (5.11 g, obtained in example 108, step 2) was added to a solution of 4-hydroxy-1-(2-methoxy-ethyl)-cyclohexanecarboxylic acid ethyl ester (5.10 g, obtained in example 2, step 3) in toluene (160 mL). The mixture was stirred for 10 minutes at RT. Then, dimethylaluminiumchloride (1M in hexane, 66.4 mL) was added dropwise over a period of 30 minutes. The reaction mixture was heated to reflux for 2 hours and then at 95° C. for 16 hours. The mixture was cooled, poured into ice/water and extracted two times with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. The title compound was obtained as an inseparable mixture of cis and trans diastereomeres as a brown oil (9.56 g, 100%). This mixture was used without further purification. MS (m/e): 345.1 [MH+].
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