Sodium Azide → tert-Butyl [1-(4-bromophenyl)cyclobutyl]carbamate

Participants

Reaction Steps

1-(4-bromophenyl)cyclobutanecarboxylic acid (7-1, 10.89 g, 42.7 mmol), Boc anhydride (10.90 mL, 47.0 mmol), sodium azide (9.71 g, 149 mmol), tetrabutylammonium bromide (2.048 mL, 6.40 mmol) and zinc trifluoromethansulfonate (0.155 g, 0.427 mmol) were stirred in THF (100 ml) at 60° for 4 h. The reaction mixture was cooled to room temperature and EtOAc and saturated aqueous sodium bicarbonate were added to the mixture. The suspension was filtered through a glass frit and the filtrate was extracted with EtOAc, washing with water and brine. The organic layer was dried over Na2SO4, filtered and reduced in vacuo to a tan oil. The crude product was purified by normal phase flash chromatography eluting with 5-15% EtOAc/Hex to give 7-2 as a white solid.

Provenance & Evidence