Hydrochloric Acid → 1-Piperidinecarboxylic acid, 4-[(2-carboxyphenyl)methyl]-, 1-(1,1-dimethylethyl) ester

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Reaction Conditions

Reaction Steps

A mixture of 4-(2-methoxycarbonyl-benzyl)-piperidine-1-carboxylic acid tert-butyl ester (330 mg; 0.99 mmol; 1 eq.) and 1M NaOH (2 mL; 2 mmol; 2 eq.) in EtOH (3 mL) was stirred at 60° C. for 16 hours. The pH was made acidic with 1M HCl and the mixture extracted with DCM (2×). The combined organic phase was dried over magnesium sulfate and concentrated in vacuo to afford the title compound (295 mg, 93%) as a white solid. HPLC (max plot) 99.8%; Rt 4.40 min. 1H NMR (300 MHz, CDCl3) δ 11.17 (s, 1H), 8.07 (dd, J=7.9, 1.5 Hz, 1H), 7.50-7.44 (m, 1H), 7.31 (td, J=7.6, 1.3 Hz, 1H), 7.21 (dd, J=7.7, 1.3 Hz, 1H), 4.07 (s, 2H), 2.98 (d, J=6.8 Hz, 2H), 2.62 (t, J=12.7 Hz, 2H), 1.80-1.57 (m, 3H), 1.45 (s, 9H), 1.28-1.14 (m, 2H).

Provenance & Evidence