(R)-(4-(1-(Benzyloxy)-3-fluoropropan-2-yl)-3-methylphenyl)boronic acid → (R)-(4-(1-Fluoro-3-hydroxypropan-2-yl)-3-methylphenyl)boronic acid

Participants

Reaction Steps

To 24C (0.2 g, 0.662 mmol) was added Pd/C (0.070 g, 0.662 mmol) and MeOH (10 mL) under N2. The reaction was flush with N2 and degassed (3×). Then H2 balloon was introduced and system was degassed and flush with H2 (3×) before letting it stir at rt overnight. The mixture was filtered and washed with MeOH (3×). The filtrate was evaporated and dried under vacuo to give 24D (0.1 g, 0.472 mmol, 71.3% yield). 1H NMR (400 MHz, MeOD) δ ppm 7.36-7.46 (m, 2H) 7.23 (d, J=7.83 Hz, 1H) 4.68-4.78 (m, 1H) 4.56-4.67 (m, 1H) 3.66-3.93 (m, 2H) 3.37-3.53 (m, 1H) 2.31-2.46 (m, 3H); 19F NMR (376 MHz, MeOD) δ ppm −229.52-−222.26 (m, 1F).

Provenance & Evidence