Synthesis
The general procedure for the synthesis of 5-(N-tert-butoxycarbonylamino)-1-pentanol from 5-amino-1-pentanol and di-tert-butyl dicarbonate is as follows:
1. 5-amino-1-pentanol (15.0 g, 145.4 mmol) was dissolved in water (140 mL) and saturated aqueous NaHCO3 solution (1.4 mL) in a 1.0 L single-necked round-bottomed flask.
2. To the above solution was slowly added a solution of di-tert-butyl dicarbonate (33.3 g, 152.7 mmol) in THF (280 mL).
3. The reaction mixture was stirred overnight at room temperature, keeping the flask open to the atmosphere.
4. Upon completion of the reaction, the reaction mixture was diluted with saturated aqueous NaHCO3 solution (90 mL) and extracted with EtOAc (400 mL).
5. The organic layer was separated, dried over anhydrous Na2SO4, filtered and the solvent evaporated to give 28.9 g (98% yield) of 5-(N-tert-butoxycarbonylamino)-1-pentanol as a clear colorless oil.
6. The purity of the product was confirmed by NMR analysis and no further purification was carried out.
Note: 5-(N-Boc-amino)-1-pentanol is also available from TCI America (Portland, OR).
References
[1] Synthesis, 1990, p. 366 - 368
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 17, p. 7892 - 7901
[3] Tetrahedron Letters, 1992, vol. 33, # 20, p. 2833 - 2836
[4] Carbohydrate Research, 1999, vol. 322, # 3-4, p. 201 - 208
[5] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 3, p. 1376 - 1392
