4-(Bromomethyl)pyridine (298 mg, 1.17 mmol) and K2CO3 (774 mg, 5.61 mmol) were added to a solution of phenol (7, Intermediate I) (300 mg, 1.12 mmol) in acetone (20 mL). The reaction mixture was stirred overnight at ambient temperature, diluted with EtOAc and water. The organic layer was washed with 5% aq. NaOH, dried over anhydrous Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography (50% EtOAc:hexane) gave (R)-tert-butyl (3-hydroxy-3-(3-(pyridin-4-ylmethoxy)phenyl)propyl)carbamate (15) as dark brown solid. Yield (0.183 g, 46%); 1H NMR (400 MHz, DMSO-d6): δ 8.61 (d, J=5.2 Hz, 2H), 7.36 (d, J=5.2 Hz, 2H), 7.28-7.24 (m, 1H), 7.03 (s, 1H), 6.96 (d, J=8.0 Hz, 1H), 6.85-6.83 (m, 1H), 5.10 (s, 2H), 4.86 (bs, 1H), 4.74-4.71 (m, 1H), 3.52-3.49 (m, 1H), 3.39 (bs, 1H), 3.19-3.12 (m, 1H), 1.86-1.77 (m, 2H), 1.45 (s, 9H); MS: m/z 359.19 [M+H]+.
