[2-(4-Amino-phenyl)-ethyl]-carbamic acid tert-butyl ester

Uses

4-[2-(Boc-amino)ethyl]aniline is used as a intermediate for chemical research.

Synthesis

General procedure for the synthesis of 4-[2-(Boc-amino)ethyl]aniline from tert-butyl N-[2-(4-nitrophenyl)ethyl]carbamate: To a solution of tert-butyl N-[2-(4-nitrophenyl)ethyl]carbamate (18.7 g, 70.30 mmol) in ethanol (200 ml), a slurry of 10% palladium-carbon (2 g) was added. Water (10 ml) was subsequently added. Anhydrous ammonium formate (44.3 g, 703 mmol) was added to the reaction system at 80°C. Triethylamine (90 ml) was added slowly. After addition, the mixture was stirred at 80 °C for 1 hour. After completion of the reaction, the mixture was allowed to cool to room temperature, filtered and concentrated under vacuum. The residue was diluted with water and extracted twice with dichloromethane. The combined organic layers were washed with water, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure to afford the target product 4-[2-(Boc-amino)ethyl]aniline as a yellow oil (13.5 g, 81% yield).

References

[1] Journal of Medicinal Chemistry, 2012, vol. 55, # 11, p. 5627 - 5631
[2] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 10, p. 2852 - 2855
[3] Patent: WO2008/13997, 2008, A2. Location in patent: Sheet 9
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 6, p. 2845 - 2854
[5] Patent: WO2006/40179, 2006, A1. Location in patent: Page/Page column 99