Diisopropylethylamine → tert-Butyl [3-(benzyloxy)cyclobutyl]carbamate

Participants

Reaction Steps

A solution of 3-(benzyloxy)cyclobutanecarboxylic acid (3.40 g, 16.49 mmol), DPPA (4.62 mL, 21.43 mmol), and diisopropylethylamine (3.73 mL, 21.43 mmol) in toluene (35 mL) under argon was warmed to 80° C. and stirred for 7 h, then cooled to RT. The mixture was cooled to 0° C. and then added slowly via canula to a suspension of potassium tert butoxide (3.70 g, 33.0 mmol) in THF (50 mL) under argon held at RT. The mixture was then stirred for 1 h and EtOAc and water were then added. The layers were separated, and the organic layer was dried (MgSO4), filtered, and concentrated to give an oil. The oil was purified by silica gel chromatography (0 to 50% EtOAc/hexane gradient) to give product as a white solid (3.42 g, 75%).

Provenance & Evidence