Synthesis
The general procedure for the synthesis of 3-(Fmoc-amino)-1-propanol from methyl 9-fluorenyl chloroformate and 3-amino-1-propanol was as follows: 3-amino-1-propanol (300 mg, 4 mmol) was dissolved in anhydrous dichloromethane (15 mL) and the reaction mixture was cooled in an ice bath. A dichloromethane solution of chloroformic acid-9-fluorenylmethyl ester (528 mg, 2 mmol) was slowly added dropwise for 30 min. Subsequently, the reaction system was warmed up to room temperature and the reaction was continued with stirring for 1.5 hours. Upon completion of the reaction, the reaction mixture was washed three times with 0.5 M hydrochloric acid solution (5 mL x 3). The organic phase was washed once more with saturated saline (5 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by rapid chromatography on silica gel (eluent: petroleum ether solution of 50% ethyl acetate) to afford the target product 3-(Fmoc-amino)-1-propanol (585 mg, 98%) as a white solid.
References
[1] Patent: CN107129455, 2017, A. Location in patent: Paragraph 0118; 0119; 0120; 0121
[2] Journal of Organic Chemistry, 2007, vol. 72, # 19, p. 7222 - 7228
[3] Synthesis, 1998, # 6, p. 859 - 866
[4] Nucleosides, Nucleotides and Nucleic Acids, 2000, vol. 19, # 8, p. 1301 - 1310
[5] Chinese Chemical Letters, 2012, vol. 23, # 8, p. 923 - 926
