Carbon Dioxide → HCID 58909210, compound

Participants

Reaction Conditions

Reaction Steps

A solution of tert-butyllithium in pentane (2.40 equiv) is added to a solution of tert-butyl 2-furylcarbamate (prepared by the method of Padwa, et al Org Synth 2000, 78, 2002, 1 equiv) in TEF at −78° C. The reaction mixture is stirred for 45 min, then solid CO2 (excess) is added and the resulting mixture is warmed to 0° C. and stirred for 30 minutes. The reaction mixture is partitioned between aqueous 1 N hydrochloric acid solution and ethyl acetate. The combined organic layers are dried over sodium sulfate and concentrated. The residue is purified by flash column chromatography (hexanes initially, grading to 100% ethyl acetate), and the polar fractions are concentrated. A solution of the residue, benzylamine (2 equiv), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1 equiv), 1-hydroxy-7-azabenzotriazole (1 equiv), and triethylamine (2 equiv) in DMF is stirred at 55° C. for 24 h. The reaction mixture is concentrated, and the residue is partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate. The combined organic layers are dried over sodium sulfate and concentrated. The residue is purified by flash column (hexanes initially, grading to 100% ethyl acetate) to give tert-butyl 3-[(benzylamino)carbonyl]-2-furylcarbamate (1-1).

Provenance & Evidence