Hydrochloric Acid → 3-((1-((Benzyloxy)carbonyl)piperidin-4-yl)oxy)-5-chloro-2-methylbenzoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of benzyl 4-(5-chloro-3-(methoxycarbonyl)-2-methylphenoxy)piperidine-1-carboxylate (0.68 g, 1.627 mmol) in tetrahydrofuran (5 mL) and methanol (15 mL) was added 3 N NaOH (2.71 mL, 8.14 mmol). The reaction mixture was stirred for 1 h, then heated at 45° C. for 3 h. The volatiles were removed in vacuo to give an aqueous residue, which was diluted with water (25 mL) and cooled (ice bath). The mixture was acidified to pH˜3-4 with 1 M HCl and stirred for 15 min. The solids were filtered, washed with water, and dried under high vacuum overnight to give 3-((1-((benzyloxy)carbonyl)piperidin-4-yl)oxy)-5-chloro-2-methylbenzoic acid (0.52 g, 1.223 mmol, 75% yield). 1H NMR δ 1.54-1.72 (m, 2H), 1.83-1.98 (m, 2H), 2.29 (s, 3H), 3.38 (br. s., 2H), 3.58-3.70 (m, 2H), 4.72 (tt, 1H), 5.09 (s, 2H), 7.24-7.46 (m, 7H), 13.28 (br. s., 1H). MS(ES) [M+H]+ 404.1.

Provenance & Evidence