Lithium Hydroxide → 1-Phenylmethanesulfonyl-azetidine-2-carboxylic acid

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Reaction Conditions

Reaction Steps

1-Phenylmethanesulfonyl-azetidine-2-carboxylic acid methyl ester (1.13 g, 4.19 mmoles) was dissolved in methanol (20 mL) and cooled to 0° C. Treatment of this solution with aqueous lithium hydroxide (7.75 mL, 1 M) was followed by warming to ambient temperature over a 3 hour period. Most of the methanol was removed in vacuo and the pH was adjusted to 1 by treatment with 1 M HCl. The product was extracted into ethyl acetate, dried over anhydrous sodium sulfate and concentrated to afford 886 g (83%) of the product as a white solid. 1H NMR (CDCl3) δ2.37–2.57 (m, 2H); 3.21–3.31 (m, 1H); 3.81 (s, 3H); 4.01 (q, 1H, J=8.6); 4.33 (d, 1H, J=13.7); 4.44 (d, 1 H, J=13.7); 4.98 (dd, 1H, 9.4, 8.6); 7.34–7.53 (series of m, 5H).

Provenance & Evidence