Cyclopentadiene → Tert-butyl 2-oxa-3-azabicyclo[2.2.1]hept-5-ene-3-carboxylate

Participants

Reaction Steps

To a solution of tert-butyl N-hydroxycarbamate (9.2 g, 69.10 mmol, 1.00 equiv) and cyclopenta-1,3-diene (20.2 g, 305.59 mmol, 4.42 equiv) in methanol (600 mL) was added of a solution of sodium periodate (17 g, 79.48 mmol, 1.15 equiv) in water (180 mL) dropwise at 0° C. with stirring in 30 min. The reaction mixture was stirred for another 30 min at 0° C. and then diluted with 600 mL of water. The solution was extracted with 3×300 mL of ethyl acetate. The combined organic layers was washed with 2×200 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give 9.1 g (67%) of tert-butyl 2-oxa-3-azabicyclo[2.2.1]hept-5-ene-3-carboxylate as a white solid. 1HNMR (400 MHz, D2O, ppm) δ 6.42 (2H, s), 5.22 (1H, s), 4.99 (1H, s), 1.99 (1H, d, J=8.4 Hz), 1.73 (1H, d, J=8.4 Hz), 1.47 (9H, s).

Provenance & Evidence