Ethyl Acetate → (1R,2R)-2-(4-aminophenyl)cyclopropane-1-carboxylic acid

Participants

Reaction Steps

A Fischer-Porter bottle containing racemic-(trans)-2-(4-nitrophenyl)cyclopropanecarboxylic acid (V-2) (4.60 g, 22.22 mmol), PtO2 (0.16 g, 0.70 mmol), ethyl acetate (70 mL) and MeOH (50 mL) was purged with N2 (3x's) then charged with 40 psig H2 at RT. After 1 h, the bottle was carefully vented and the suspension was filtered through Celite. The solution was concentrated to give the title compound as a white powder (4.01 g, ˜100%). 1H NMR (400 MHz, DMSO) δ 6.79 (d, J=8.6 Hz, 2H), 6.47 (d, J=8.6, 2H), 5.02 (bs, 2H), 2.21-2.16 (m, 1H), 1.61-1.56 (m, 1H), 1.31-1.28 (m, 1H), 1.19-1.14 (m, 1H). ES-MS m/z 176.3 (MH−).

Provenance & Evidence