Hydroxyamine hydrochloride → 3-Azetidinecarboxylic acid, 1-[4-[(hydroxyimino)methyl]phenyl]-, methyl ester

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Reaction Steps

To a stirred suspension of 1-(4-formyl-phenyl)-azetidine-3-carboxylic acid methyl ester (Preparation 9, 2.6 g, 11.87 mmol) in methanol (25 mL) and water (25 mL) was added sodium acetate (1.75 g, 21.36 mmol) followed by hydroxylamine hydrochloride (1.24 g, 17.80 mmol) at 0° C. Resulting reaction mixture was stirred at room temperature for 3 hours. After consumption of starting material, methanol was evaporated under reduced pressure and extracted with EtOAc (4×30 mL). Combined organic layer was dried over anhydrous sodium sulphate and concentrated in vacuo to afford yellow colored solid (2.86 g, 99%). 1H NMR (400 MHz, CDCl3) δ: 3.55-3.59 (m, 1H), 3.75 (s, 3H), 4.05-4.13 (m, 4H), 6.42 (d, 2H, J=8.56 Hz), 7.41 (d, 2H, J=8.6 Hz), 8.03 (s, 1H); LC-MS (M+H): =235.00.

Provenance & Evidence