Lithium hydroxide, monohydrate → HCID 58611848, compound

Participants

Reaction Steps

To a solution of methyl 4-[1-(tert-butoxycarbonyl)cyclohexyl]benzoate (1) (0.273 g, 0.86 mmol) in tetrahydrofuran (5 ml) was added 0.63 N LiOH water solution (3 ml, 1.89 mmol) and the resultant suspension was stirred at ambient temperature for 5 days. The reaction mixture was diluted with water (20 ml) and saturated NaH2PO4 (5 ml), and the obtained suspension was extracted with ethyl acetate (2×30 ml). The extract was washed with brine (15 ml), dried (Na2SO4), and the solvent was removed in vacuo. The residue was chromatographed on silica gel with toluene-ethyl acetate-acetic acid (8:2:01) as eluent to give the title compound (0.231 g, 88%) as a white solid. 1H NMR (CDCl3, HMDSO) δ: 1.07-1.91 (8H, m); 1.35 (9H, s); 2.20-2.63 (2H, m); 7.52 (2H, d, J=8.5 Hz); 8.06 (2H, d, J=8.5 Hz); 11.20 (1H, br s).

Provenance & Evidence