HCID 59464121, compound → HCID 178471531, compound

Participants

Reaction Steps

Platinum oxide (300 mg) was added in one portion to a stirred solution of ethyl 2-[4-(4-{[(benzyloxy)carbonyl]amino}-3-chlorophenyl)cyclohexylidene]propanoate (1.7 g, 3.85 mmol) in ethyl acetate (50 mL) and the mixture was stirred at room temperature under a hydrogen atmosphere for 9 h. The reaction mixture was filtered and concentrated in vacuo to leave a residue, which was purified by column chromatography, using a gradient of 11-66% ethyl acetate:isohexane as eluent, to give the aniline product as a mixture of cis- and trans-cyclohexane isomers. Recrystallisation from a mixture of ethanol and diethyl ether gave the title compound (0.37 g, 28%) as a white solid; 1H NMR δ 1.08 (3H, d), 1.2-1.3 (1H, m), 1.27 (3H, t), 1.31-1.49 (1H, m), 1.52-1.7 (1H, m), 1.71-1.81 (1H, m), 1.81-1.97 (3H, m), 2.2-2.32 (1H, m), 2.33-2.48 (1H, m), 4.15 (2H, dq), 7.02 (1H, dd), 7.2 (1H, d), 7.22 (1H, d); MS m/e MH+ 310.

Provenance & Evidence