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

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Reaction Steps

A solution of 4-ethoxycarbonylmethyl-piperazine-1-carboxylic acid tert-butyl ester (1.3 g, 4.78 mmol) in methanol (50 ml) was treated with NaOH (1N, 10 ml, 10 mmol) and stirred for 4 h. The mixture is concentrated and the residue is adjusted to pH 6 with 5% citric acid solution. The mixture is extracted with ethyl acetate, dried over sodium sulfate and concentrated to give 4-carboxymethyl-piperazine-1-carboxylic acid tert-butyl ester, 445 mg (38%) as a white solid. ESI MS m/z 1179 (M+H+); 1H NMR (400 MHz, CDCl3) δ 3.80-3.60 (m, 4H), 3.42 (s, 2H), 3.10-2.84 (m, 4H), 1.24 (s, 9H).

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