Triethylamine → 2-Dimethylcarbamoyl-5-methyl-hexahydro-cyclopenta[c]pyrrole-5-carbonylazide

Participants

Reaction Steps

Upon cooling by an ice-water bath, 2-dimethylcarbamoyl-5-methyl-octahydro-cyclopenta[c]pyrrole-5-carboxylic acid 12c (1.0 g, 4.2 mmol) was dissolved in 25 mL of acetone with stirring, followed by dropwise addition of a solution of triethylamine (463.5 mg, 4.58 mmol) and ethyl chloroformate (497 mg, 4.58 mmol) in 10 mL of acetone at −5° C. The reaction mixture was reacted for 15 minutes at −5° C. followed by addition of a solution of sodium azide (546 mg, 8.4 mmol) in 10 mL of water. Then the reaction mixture was stirred for another 30 minutes at −5° C., and quenched with 25 mL of water and extracted with ethyl acetate (50 mL×3). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude compound 2-dimethylcarbamoyl-5-methyl-hexahydro-cyclopenta[c]pyrrole-5-carbonylazide 12d (700 mg) as a yellow oil.

Provenance & Evidence