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

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.

1. temperatureThe reaction mixture was cooled in an ice bath
2. custombefore quenching with saturated aqueous sodium bicarbonate solution
3. customThe layers were separated
4. extractionextracted with ethyl acetate (3×)
5. dry with materialThe combined organic extracts were dried (MgSO4)
6. filtrationfiltered
7. customevaporated under reduced pressure

ORD record

ord-206f0169abc94454bc9ed6c71b5c151f

Source dataset

uspto-grants-2003_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06586430B1