Ammonia → tert-Butyl 3-carbamoylazetidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To 1.0 g (4.97 mmol) boc-azetidine-3-carboxylic acid in 10 mL anhydrous THF was added 0.55 mL of 1-methyl-2-pyrrolidinone. The reaction mixture was cooled to −20° C., then 0.62 mL (4.72 mmol) isobutyl chloroformate was added and the reaction was stirred for 5 minutes. 1.51 mL (24.85 mmol) aqueous ammonia (28% w/w) was added and the mixture was stirred at −20° C. for 2 hours. 5 mL aqueous NaHCO3 (1 M) was added and the mixture was allowed to reach room temperature over 1 hour. The mixture was extracted with DCM (3×10 mL), the organic layers were combined, washed with aqueous NaHCO3 (1 M), aqueous citric acid (1 M) and dried over Na2SO4. After filtration and evaporation of the solvent the product was used in the next step without further purification.

Provenance & Evidence