Nitrogen → 3-(3-Oxocyclobutyl)propanoic acid

Participants

Reaction Steps

A solution of 3-(3-Oxo-cyclobutyl)-propionic acid benzyl ester (9) (8.12 g, 34.96 mmol) in ethyl acetate (80 ml) was purged 3× with N2 before 10% Pd/C (800 mg, 0.077 mmol, ˜2 mol %) was added. The reaction mixture was purged again 3× with N2 then twice with H2 before leaving the reaction under an atmosphere of H2. The reaction was monitored by LCMS until no more sign of starting material was observed (˜10 h). The reaction was purged with 3 times N2, filtered through celite and Pd/C was washed 3× with ˜25 ml of EtOAc. The combined organic were concentrated to yield 4.94 g (99%) of 10 as a light yellow oil. NMR analysis shows clean product, no further purification was required. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 11.46 (1 H, br. s.), 3.09-3.29 (2 H, m), 2.63-2.80 (2 H, m), 2.35-2.53 (3 H, m), 1.95 (2 H, q, J=7.57 Hz).

Provenance & Evidence