Benzyl Alcohol → Benzyl 1-benzylaziridine-2-carboxylate

Participants

Reaction Steps

To a solution of 2,3-dibromopropionyl chloride (5.00 g, 19.97 mmol) in THF (25 ml) at 0° C. was added dropwise benzyl alcohol (2.10 ml, 19.97 mmol). After stirring for 1 h, the reaction was concentrated in vacuo and the resulting oil dissolved in CH2Cl2 (25 ml) and treated with a solution of benzyl amine (2.20 ml, 19.97 mmol) and TEA (5.80 ml, 41.94 mmol) in CH2Cl2 (10 ml) at 0° C. After stirring for 3 h, the reaction was filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluted with hexane/ethyl acetate (4:1) to afford N-benzyl-aziridine-2-carboxylic acid, benzyl ester as a colorless oil (2.35 g).

Provenance & Evidence