Sulfuric Acid → 1-Benzhydryl-3-hydroxy-azetidine-3-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

1-Benzhydryl-3-(trimethylsilyloxy)azetidine-3-carbonitrile (2.85 g, 8.47 mmol) was taken up in a 1:1 mixture of 1,4-dioxane (30 mL) and 60% aqueous sulfuric acid (30 mL). The mixture was heated to 95° C. for 1 h. The solvent was removed and the residue was taken to pH 7 using 5N NaOH. The solid was isolated by filtration, rinsed with Et2O to give 1-benzhydryl-3-hydroxyazetidine-3-carboxylic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.36-7.47 (m, 4H), 7.22-7.33 (m, 4H), 7.13-7.23 (m, 2H), 4.52 (s, 1H), 3.46 (d, J=8.3 Hz, 2H), 3.02 (d, J=8.2 Hz, 2H). MS (ESI) m/z: Calculated; 283.1 Observed: 284.1 (M++1).

Provenance & Evidence