To a solution of tert-butyl 4-(adamantan-2-yl(hydroxy)methyl)-3-chlorobenzoate (0.32 mg, 1.00 mmol) in anhydrous dimethylformamide (5 mL) was added sodium hydride (60% dispersion in mineral oil, 0.048 g, 1.2 mmol) at 0° C. The reaction mixture was allowed to warm to ambient temperature and stirred for 1 hour. Benzyl bromide (0.24 mL, 2.00 mmol) and tetrabutylammonium iodide (0.037 g, 0.10 mmol) was added and the reaction mixture was stirred for 16 hours at ambient temperature. After quenched with saturated ammonium chloride solution (10 mL), the mixture was diluted with ethyl acetate (150 mL). The organic phase was washed with water (3×10 mL), brine (10 mL), dried over anhydrous sodium sulfate, and filtered. Concentration of the filtrate in vacuo gave a residue which was purified by silica gel column chromatography using 0-20% ethyl acetate in hexanes as eluent to afford the title compound as a colorless oil (0.437 g, quant.): 1H NMR (300 MHz, CDCl3) δ 7.97-7.95 (m, 1H), 7.90 (d, J=8.18 Hz, 1H), 7.60 (d, J=7.39 Hz, 1H), 7.46-7.18 (m, 5H), 5.18-5.11 (m, 1H), 4.30 (d, J=11.54 Hz, 1H), 4.18 (d, J=11.60 Hz, 1H), 2.41 (s, 1H), 2.12-1.30 (m, 22H), 1.13 (s, 1H).
