Tert-Butanesulfinamide → tert-Butyl 3-(((tert-butylsulfinyl)imino)methyl)azetidine-1-carboxylate

Participants

Reaction Steps

To a solution of 3-formyl-azetidine-1-carboxylic acid tert-butyl ester (1.0 g, 5.4 mmol) and 2-methylpropane-2-sulfinamide (654 mg, 5.4 mmol) in dry CH2Cl2 (10 mL) was added anhydrous CuSO4 (1.9 g, 11.9 mmol). The heterogeneous reaction mixture was stirred at room temperature overnight then filtered over Celite, rinsing with CH2Cl2. The filtrate was concentrated and the resultant residue was absorbed onto SiO2 and purified by column chromatography with 20% to 40% EtOAc/hexanes to provide 1.26 g (81%) of 3-{[(E)-2-methyl-propane-2-sulfinylimino]-methyl}-azetidine-1-carboxylic acid tert-butyl ester as a white solid.

Provenance & Evidence