CN(OC)[C:3](=[O:19])[CH2:4][CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.[F:22][C:23]1[CH:28]=[CH:27][C:26]([Mg]Br)=[CH:25][CH:24]=1.COCCOC.CCOC(C)=O>CCOCC>[F:22][C:23]1[CH:28]=[CH:27][C:26]([C:3](=[O:19])[CH2:4][CH2:5][CH:6]2[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:10][CH2:11]2)=[CH:25][CH:24]=1N-Methyl-N-methoxy-3-(1-(tert-butoxycarbonyl)piperidin-4-yl)propionamide (550 mg, 1.83 mmol, from Step B) was dissolved in 10 mL dry ether and the solution was cooled to 0° C. A solution of 4-fluorophenyl magnesium bromide (2 mL, 1.0 M in THF, 2.01 mmol) was added dropwise. A solid mass formed upon addition and 1 mL 1,2-dimethoxyethane was added. The mixture was warmed to room temperature and stirred for 45 min then poured into 100 mL EtOAc/10 mL 1 M aqueous HCl. The layers were separated and the organic phase was washed with water, then sat'd NaCl, then dried over Na2SO4 and concentrated. Flash chromatography (25 grams silica, 5/1 hexane/EtOAc eluant) afforded 423 mg (69%) of the title compound. 1H NMR (300 MHz, CDCl3) δ1.0-1.20 (m, 2H), 1.45 (s, 9H), 1.65-1.75 (m 4H), 2.6-2.75 (m 2H), 2.9-3.0 (t, 2H), 4.03-4.08 (m, 2H), 7.1-7.19 (m, 2H), 7.95-8.04 (m, 2H).
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