Dimethylformamide → 3-(2-Chloro-4-nitrophenyl)-1,3-diazaspiro[4.6]undecane-2,4-dione

Participants

Reaction Steps

A mixture of 1-aminocycloheptanecarboxylic acid (125 mg, 0.8 mmol) and DMF (0.8 mL) was treated with DBU (0.119 mL, 0.8 mmol) and allowed to stir for 5 min. The solution was then treated with 2-chloro-4-nitrophenylisocyanate (237 mg, 1.2 mmol) in DCE (2 ml) and the resulting mixture was allowed to stir for 30 min at ambient temperature and then reacted in a microwave vessel at 160° C. for 10 min. The reaction mixture was then cooled to rt, diluted with CH2Cl2 and then extracted with water, 1N HCl, sat. aq. NaHCO3, and the solvent removed under reduced pressure. The crude residue was re-crystallized from hot MeOH to afford 51 mg of 3-(2-chloro-4-nitrophenyl)-1,3-diazaspiro[4.6]undecane-2,4-dione, 1.1.15, (18%).

Provenance & Evidence