Acetic Acid → HCID 178464369, compound

Participants

Reaction Steps

A stirred suspension of methyl trans-4-[(ethylamino)carbonyl]cyclohexanecarboxylate (Intermediate 5, 430 mg, 2.01 mmol) and NaBH4 in THF (10 mL) was treated with acetic acid (1.6 mL) and heated at reflux for 16 h an atmosphere of N2. The reaction was cooled to room temperature, quenched with H2O (1 mL) and diluted with 1N NaOH (15 mL). The mixture was extracted with EtOAc (3×40 mL) and the combined extracts were washed with brine (40 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash silica gel chromatography (0-25% EtOAc/hexanes gradient) to afford methyl trans-4-[(ethylamino)methyl]cyclohexanecarboxylate as a clear oil. LCMS=200.2 (M+)+. 1H NMR (CDCl3, 500 MHz): δ 3.67 (s, 3H), 2.67-2.64 (q, J=7.1 Hz, 2H), 2.49-2.46 (m, 2H), 2.28-2.24 (m, 1H), 2.16-1.86 (m, 4H), 1.49-1.41 (m, 2H), 1.12 (t, J=5.5 Hz, 3H), 1.03 (m, 2H).

Provenance & Evidence