Synthesis
The synthesis of tert-butyl N-allylcarbamate was carried out as follows:
1. 2.3 mL (30 mmol, 1 eq.) of freshly distilled allylamine was dissolved in 10 mL of dichloromethane (CH2Cl2) in an ice bath (0 °C).
2. 6.54 g (30 mmol, 1 eq.) of di-tert-butyl dicarbonate (Boc2O) dissolved in 20 mL of dichloromethane was slowly added to the above cooled allylamine solution.
3. The reaction mixture was gradually warmed to room temperature with continuous stirring for 4 hours.
4. Upon completion of the reaction, the reaction mixture was diluted with additional dichloromethane and washed sequentially with 5% citric acid solution and brine.
5. The organic layer was separated and dried over anhydrous sodium sulfate (Na2SO4) and subsequently concentrated under vacuum to afford 3.29 g (68% yield) of the target product tert-butyl N-allylcarbamate.
Product characterization data: 1H NMR (500 MHz, CDCl3) δ 1.38 (s, 9H), 3.68 (brs, 2H), 4.53 (brs, 1H), 5.02-5.16 (m, 2H), 5.72-5.84 (m, 1H).
References
[1] Tetrahedron Letters, 2007, vol. 48, # 35, p. 6163 - 6166
[2] Angewandte Chemie - International Edition, 2014, vol. 53, # 41, p. 11075 - 11078
[3] Tetrahedron Letters, 1998, vol. 39, # 15, p. 2099 - 2102
[4] Journal of the Chemical Society. Perkin Transactions 1, 2001, # 16, p. 1916 - 1928
[5] Tetrahedron Letters, 2009, vol. 50, # 46, p. 6244 - 6246
