Reaction Steps
Example 8 was prepared from methyl 3-((R)-4-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-4-oxobutan-2-ylcarbamoyl)benzoate using the conditions described in Example 6. MS (ESI+)=473.2 (M+H)+. 1H NMR (CD3OD, 500 MHz) (NMR shows several rotamers) δ ppm 8.54 (t, J=1.6 Hz, 0.6 H), 8.46 (t, J=1.6 Hz, 0.4 H), 8.22 (d, J=7.7 Hz, 0.6 H), 8.17 (d, J=7.7 Hz, 0.4 H), 8.08 (d, J=8.2 Hz, 0.6 H), 8.02 (d, J=7.7 Hz, 0.4 H), 7.61 (t, J=7.7 Hz, 0.6 H), 7.57 (t, J=7.7 Hz, 0.4 H), 7.47 (d, J=8.8 Hz, 0.8 H), 7.32-7.25 (m, 2 H), 7.23 (d, J=8.3 Hz, 1.2 H), 4.64-4.46 (m, 1.4 H), 4.10 (dt, J=13.2, 2.5 Hz, 0.6 H), 4.04 (dd, J=12.6, 2.2 Hz, 0.6 H), 3.67-3.53 (m, 1.4 H), 3.17-3.03 (m, 1.6 H), 2.97 (dd, J=14.9, 6.1 Hz, 0.4 H), 2.67-2.46 (m, 2 H), 1.57-1.47 (m, 1 H), 1.40 (d, J=6.6 Hz, 1.8 H), 1.34 (d, J=6.6 Hz, 1.2 H), 0.83 (s, 1.2 H), 0.82 (s, 1.2 H), 0.76 (s, 1.8 H), 0.66 (s, 1.8 H); HPLC Method: Inj. Vol.=5 uL, Start % B=10, 12 Min. 100%, 15 Min. 100%, Flow Rate=1 ml/min, Wavelength 1=220, Wavelength 2=254, Solvent A=0.05% TFA in H2O:MeCN (95:5), Solvent B=0.05% TFA in H2O:MeCN (5:95), Col-1: Sunfire C18 3.5 um, 4.6×150 mm; Retention Time=10.92 min., Col-2: Xbridge Phenyl 3.5 um, 4.6×150 mm; Retention Time=10.45 min.
