tert-butyl N-ethenylcarbamate

1321892-09-4

7150-72-3

The general procedure for synthesizing N-Boc-vinylamine from the compound (CAS:1321892-09-4) was as follows: first, a THF solution of DMAP (0.05 equiv, 0.436 g, 3.57 mmol) was prepared by dissolving DMAP (0.05 equiv, 0.436 g, 3.57 mmol) in THF (12.8 mL) under dry conditions. Subsequently, N-vinylformamide (5.07 g, 5 mL, 71.3 mmol) was added to the above stirred DMAP solution. Next, a THF (25 mL) solution of Boc2O (1.2 equiv, 18.7 g, 18.3 mL, 85.6 mmol) was slowly added dropwise to the reaction mixture. Bubbles were observed during the reaction and the color of the mixture changed to yellow. The progress of the reaction was monitored by TLC (unfolding agent ratio 80:20 petroleum ether:ethyl acetate) and after confirming that the substrate was completely consumed, the reaction mixture was diluted with water and petroleum ether. The organic phase was separated and washed twice with water and subsequently dried over MgSO4, filtered and concentrated under reduced pressure. The crude product intermediate obtained was dissolved directly in THF (45 mL) without further purification and the solution was cooled to 0 °C. An aqueous NaOH solution (1.2 equiv, 2M, 42.8 mL, 85.6 mmol) was slowly added to the reaction mixture over a period of 20 min. After completion of the reaction (monitored by TLC with a spreading agent ratio of 80:20 petroleum ether:ethyl acetate), the reaction mixture was diluted with tBuOMe and water, and the organic layer was separated and washed with water. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was crystallized at 0 °C and subsequently dissolved in a minimal amount of pentane, and the target product tert-butyl phenyl carbamate (7.57 g, 52.9 mmol, 74% yield) was obtained by recrystallization from pentane.