Phosgene → HCID 57786802, compound

Participants

Reaction Steps

Phosgene (20% in toluene, 0.26 mL, 0.49 mmol) was added to a solution of 2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (0.096 g, 0.411 mmol) and diisopropylethylamine (0.29 mL, 1.7 mmol) in 4 mL of dichloromethane at 0-5° C. The reaction mixture was then stirred at RT for 30 min., then transferred via Pasteur pipette to a flask containing 3-(2,2,2-trifluoro-1-trifluoromethyl-ethoxy)-azetidine hydrochloride prepared as in the above example (0.41 mmol). A total of 6 mL of additional dichloromethane was used in rinsing. The very pale yellow solution was stirred for 18.5 h. 10 g of silica gel was added, and the mixture was concentrated to a white powder. Column chromatography (0->50% EtOAc/hexanes) afforded 0.117 g (59%) of 3-(2,2,2-trifluoro-1-trifluoromethyl-ethoxy)-azetidine-1-carboxylic acid [2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amide as a colorless oil.

Provenance & Evidence