Triethylamine → 5-Cyclohexylmethyl-2-dimethylcarbamoyl-octahydro-cyclopenta[c]pyrrole-5-carbonyl azide

Participants

Reaction Steps

Upon cooling by an ice-water bath, 5-cyclohexylmethyl-2-dimethylcarbamoyl-octahydro-cyclopenta[c]pyrrole-5-carboxylic acid 15c (0.75 g, 2.33 mmol) was dissolved in 20 mL of acetone with stirring followed by dropwise addition of triethylamine (0.36 mL, 2.56 mmol) and a solution of 2 mL of ethyl chloroformate (0.25 mL, 2.56 mmol) in acetone. The reaction mixture was stirred for 15 minutes and a solution of 2 mL of sodium azide (0.303 g, 4.66 mmol) in water was added. The reaction mixture was reacted for another 30 minutes at 0° C.˜−5° C. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was concentrated to remove acetone and diluted with 10 mL of water. The mixture was extracted with ethyl acetate (10 mL×5). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain the title compound 5-cyclohexylmethyl-2-dimethylcarbamoyl-octahydro-cyclopenta[c]pyrrole-5-carbonyl azide 15d (0.79 g) as a yellow oil which was directly used in the next step.

Provenance & Evidence