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

Participants

Reaction Steps

A solution of 3-azetidine carboxylic acid (0.50 g, 4.9 mmol), trimethylsilyl chloride (1.25 ml, 9.8 mmol) and N-ethyldiisopropylamine (2.20 ml, 12.6 mmol) was heated under reflux in dichloromethane (20 ml) for 20 minutes. The reaction mixture was cooled in an ice bath and benzyl chloroformate (0.92 ml, 6.4 mmol) added. The mixture was stirred at room temperature for 72 hours before quenching with saturated aqueous sodium bicarbonate solution. The layers were separated and the aqueous phase was acidified to pH2 with 2N hydrochloric acid and extracted with ethyl acetate (3×). The combined organic extracts were dried (MgSO4), filtered and evaporated under reduced pressure to afford the title compound as a brown oil, 1.01 g.

Provenance & Evidence