Synthesis
GENERAL METHODS: To a solution of N-Boc-N'-Cbz-L-lysine (10 mmol) in THF (10 mL) was added DIPEA (11 mmol, 1.42 mL) and EtOAc solution of 50% T3P (20 mmol, 6.36 mL) at 0 °C with stirring for about 10 min. Then NaBH4 aqueous solution (10 mmol, 388 mg, dissolved in 0.3 mL H2O) was slowly added to the reaction mixture at the same temperature, and the progress of the reaction was monitored by TLC until the reaction was completed. After completion of the reaction, the solvent was removed by evaporation under reduced pressure and the crude product was extracted with EtOAc. The organic phase was washed sequentially with 5% aqueous citric acid (10 mL × 2), 5% aqueous Na2CO3 (10 mL × 2), water and saturated saline. The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to give (S)-tert-butylbenzyl (6-hydroxyhexane-1,5-diyl) dicarbamate.
References
[1] Tetrahedron Asymmetry, 2015, vol. 26, # 21-22, p. 1273 - 1280
[2] Tetrahedron Letters, 2012, vol. 53, # 38, p. 5059 - 5063
[3] Synlett, 1999, # 8, p. 1239 - 1240
[4] Chemical and Pharmaceutical Bulletin, 1982, vol. 30, # 5, p. 1921 - 1924
[5] Tetrahedron Letters, 1991, vol. 32, # 7, p. 923 - 926
