N-Boc-1,3-diaminopropane is used in the preparation of spermidine analogues as well as in the preparation of pharmacologically active compounds. It is also used in suzuki reaction. Further, it is used in the preparation of [3-(3-cyano-propylamino)-propyl]-carbamic acid tert-butyl ester.
GENERAL PROCEDURE: To a suspension of 1,3-propanediamine (20.0 g, 172 mmol) in 50 mL of dichloromethane (DCM) cooled to 0°C, a solution of di-tert-butyl dicarbonate (Boc2O, 3.75 g, 17.2 mmol) in 24 mL of DCM was slowly added. After addition, the ice bath was removed and the reaction mixture was stirred at room temperature for 18 hours. After completion of the reaction, the precipitate was removed by filtration and the filtrate was washed sequentially with saturated aqueous sodium bicarbonate (NaHCO3) (3 x 50 mL), water (2 x 50 mL) and brine (50 mL). The organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to give an oily product N-tert-butoxycarbonyl-1,3-propanediamine 3.1 g in 84% yield.
[1] Journal of Organic Chemistry, 1997, vol. 62, # 2, p. 411 - 416
[2] Liebigs Annales, 1996, # 6, p. 935 - 939
[3] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 4, p. 1009 - 1018
[4] Organic and Biomolecular Chemistry, 2015, vol. 14, # 2, p. 455 - 459
[5] New Journal of Chemistry, 2018, vol. 42, # 12, p. 10142 - 10147
