Diisopropylcarbodiimide → HCID 57951456, compound

Participants

Reaction Steps

N,N′-diisopropylcarbodiimide (96 mg, 0.76 mmol) was added to a solution of 3-methyl-1-oxa-2-azaspiro[4.5]dec-2-ene-8-carboxylic acid (150 mg, 0.76 mmol) in DCM (40 ml). The reaction mixture was mixed after 30 minutes with 1-hydroxybenzotriazole hydrate (HOBt, 101 mg, 0.76 mmol) and tert-butylaniline (113 mg, 0.76 mmol), stirred overnight and the solvent removed under vacuum. The residue was taken up in EtOAc. The organic phase was washed successively with diluted aq. citric acid solution and sat. aq. NaCl solution, dried over magnesium sulphate and the solvent removed under vacuum. The desired product N-(4-tert-butylphenyl)-3-methyl-1-oxa-2-azaspiro[4.5]dec-2-ene-8-carboxamide was obtained after purification by column chromatography (SiO2, hexane/EtOAc 1:1) as a diastereomer mixture in a yield of 66 mg.

Provenance & Evidence