Benzyl chloroformate → 1-[(Benzyloxy)carbonyl]azetidine-3-carboxylic acid

Participants

Reaction Steps

To a solution of azetidine-3-carboxylic acid (5.00 g, 49.5 mmol) in dioxane (325 ml) were added 1N sodium hydroxide (124 ml, 124 mmol) and benzyl chloroformate (8.44 ml, 59.3 mmol). The reaction was allowed to stir for 18 h. The reaction was diluted with 3N HCl until pH 2 was obtained. The product was extracted with EtOAc (2×), washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude material was purified via flash chromatography (silica, 0-70% methanol (0.5% acetic acid)/dichloromethane) to yield 1-[(benzyloxy)carbonyl]azetidine-3-carboxylic acid as a yellow oil (73%). 1H NMR (400 MHz, CD3OD) δ 7.37-7.26 (m, 5H), 5.08 (s, 2H), 4.18 (m, 2H), 4.11 (br s, 2H), 3.44 (m, 1H).

Provenance & Evidence