3,3-Difluoro-1-((2-methoxy-4-nitrophenoxy)methyl)cyclobutanol → 1-((4-Amino-2-methoxyphenoxy)methyl)-3,3-difluorocyclobutanol

Participants

Reaction Steps

A mixture of 3,3-difluoro-1-((2-methoxy-4-nitrophenoxy)methyl)cyclobutanol (32.0 g, 111 mmol) prepared in Part F and 10% Pd/C (2.0 g, 1.879 mmol) in 700 mL MeOH was stirred under H2 at 50 psi for 1.5 h. After filtration, the filtrate was concentrated to give 1-((4-amino-2-methoxyphenoxy)methyl)-3,3-difluorocyclobutanol (28.9 g, 111 mmol, quantitative yield) as a light purple solid. 1H NMR (400 MHz, CD3OD) δ ppm 6.68 (1H, d, J=8.56 Hz), 6.35 (1 H, d, J=2.52 Hz), 6.16 (1 H, dd, J=8.31, 2.52 Hz), 4.77 (3 H, br. s.), 3.78 (2 H, s), 3.68 (3 H, s), 2.68-2.82 (2 H, m), 2.38-2.56 (2 H, m).

Provenance & Evidence