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To a room temperature solution of [1-(4-Chloro-phenyl)-cyclobutyl]-(3-hydroxymethyl-azepan-1-yl)-methanone (0.3307 g, 1.15 mmol) in tetrahydrofuran (5.75 mL, 0.2M) under N2 was added triphenyl phosphine (0.9050 g, 3.45 mmol) and 4-trifluoromethylphenol (0.56 mL, 3.45 mmol). The solution was cooled to 0° C., then diethyl azodicarboxylate (0.54 mL, 3.1 mmol) was added dropwise over 10 minutes. When the reaction was complete by H PLC (2 hours), ethyl acetate and 10% aqueous NaOH was added. The organics were removed, dried with Na2SO4, concentrated, then taken up in Hexanes/ethyl acetate (70:30) and filtered to remove triphenyl phosphine oxide. The remaining yellow oil was purified by silica gel chromatography (3:1 to 2:3 Hexanes:ethyl acetate). The product was further purified by silica gel chromatography with 9:1 hexanes:ethyl acetate to obtain pure product in 26% yield (0.1301 g). Partial 1H NMR (CDCl3, 300 MHz) 7.55 (2H, t, J=8.7 Hz), 7.36-7.26 (4H, m), 6.92 (2H, dd, J=34.9, 8.7 Hz), 4.00-3.85 (2H, m), ppm. Partial 13C NMR (CDCl3, 75 MHz) 174.95, 161.66, 142.17, 132.35, 129.10, 126.95, 126.77, 114.61, 114.61, 71.50, 71.10 ppm. LRMS: 465.26.

1. additionwas added
2. customThe organics were removed
3. dry with materialdried with Na2SO4
4. concentrationconcentrated
5. filtrationfiltered
6. customto remove triphenyl phosphine oxide
7. customThe remaining yellow oil was purified by silica gel chromatography (3:1 to 2:3 Hexanes:ethyl acetate)
8. customThe product was further purified by silica gel chromatography with 9:1 hexanes
9. customethyl acetate to obtain pure product in 26% yield (0.1301 g)