Benzophenone imine → tert-Butyl 3-(6-(Diphenylmethyleneamino)pyridin-3-yl)azetidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A 500-mL round-bottomed flask equipped with a magnetic stirrer and reflux condenser was charged with 117a (2.00 g, 7.46 mmol), benzophenoneimine (1.62 g, 8.96 mmol), sodium tert-butoxide (1.00 g, 10.4 mmol), (dibenzylideneacetone)-dipalladium(0) (340 mg, 0.373 mmol) and rac-2,2′-bis(diphenylphosphino)-1,1′-binapthyl (700 mg, 1.12 mmol), and the reaction was heated at 100° C. for 3 h. After this time the reaction was cooled to room temperature and concentrated under reduced pressure. The resulting oil was purified by column chromatography to afford a 79% yield (2.44 g) of 117b as a brown solid: mp 104-105° C.; 1H NMR (500 MHz, CDCl3) δ 8.20 (d, 1H, J=2.0 Hz), 7.85 (br s, 2H), 7.52 (br s, 1H), 7.44 (br s, 2H), 7.47 (dd, 1H, J=8.5, 2.0 Hz), 7.17 (br s, 5H), 6.61 (d, 1H, J=8.5 Hz), 4.30 (t, 2H, J=8.5 Hz), 3.86 (dd, 2H, J=8.5, 4.5 Hz), 3.62 (m, 1H), 1.45 (s, 9H); MS (ESI+) m/z 413.8 (M+H).

Provenance & Evidence