Lithium Hydroxide → 2-{4-[(Tert-butoxy)carbonyl]piperazin-1-yl}acetic acid

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Reaction Steps

Combine 1-t-butoxycarbonyl-4-carboethoxymethylpiperazine (20.8 g, 76.5 mmol) and lithium hydroxide (6.71 g, 160 mmol) in tetrahydrofuran (100 mL) and water (100 mL). After 60 minutes, concentrate in vacuo to give a solid. Combine the solid and water, extract with diethyl ether. Combine the aqueous layer and a 1M aqueous solution of potassium hydrogensulfate (160 mL). Extract three times with chloroform. Evaporate the aqueous layer to give a solid. Triturate the solid repeatedly with warm ethyl acetate and isopropanol and filter. Evaporate each triturate to give solids. Combine the solids obtained by evaporation of the triturates, dissolve in chloroform and evaporate to remove solvent. Dry in vacuo at 50° C. to give 1-t-butoxycarbonyl-4-carboxymethylpiperazine as a solid, mp: 195-197° C. IR (KBr) nmax 3007, 2934, 1691, 1631, 1479, 1453, 1427, 1415, 1393, 1366, 1301, 1283, 1232, 1209, 1177, 1139, 1084 cm-1 ; 1H NMR (CDCl3) ppm 3.71 (br s, 4 H), 3.56 (br s, 2 H), 3.12 (br s, 4 H), 1.46 (s, 9 H); 13C NMR (CDCl3) ppm 169.10, 154.13, 80.70, 58.49, 52.38, 28.25; MS (CI/NH3) m/z 245 (M+1)+.

Provenance & Evidence