Phenol → (R)-tert-butyl (3-hydroxy-3-(3-(pyridin-4-ylmethoxy)phenyl)propyl)carbamate

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]+.

1. washThe organic layer was washed with 5% aq. NaOH
2. dry with materialdried over anhydrous Na2SO4
3. concentrationconcentrated under reduced pressure
4. customPurification by flash chromatography (50% EtOAc:hexane)

ORD record

ord-5f61ca2ffa284be2ae3d72df76ceea38

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133154B2