Synthesis
GENERAL STEPS: 10 g (133 mmol) of (R)-2-aminopropan-1-ol and 14.8 g (146.5 mmol) of triethylamine were dissolved in 500 mL of tetrahydrofuran and the solution was cooled to 0 °C. A one-time addition of 30 g (133 mmol) of di-tert-butyl dicarbonate was added to the solution with stirring. The reaction mixture was stirred at room temperature for about 18 hours. Upon completion of the reaction, the mixture was concentrated under reduced pressure to remove the solvent. The residue was dissolved in 300 ml of ethyl acetate and washed twice sequentially with 200 ml of water and once with 200 ml of saturated aqueous sodium chloride. The organic layer was dried with magnesium sulfate, filtered and concentrated under reduced pressure to give 22 g (94% yield) of the target product N-Boc-L-alaninol as a yellow oil. The structure of the product was confirmed by 1H-NMR (CDCl3): δ4.71 (multiple peaks, 1H), 3.72 (multiple peaks, 1H), 3.59-3.46 (multiple peaks, 2H), 2.86 (multiple peaks, 1H).
References
[1] Tetrahedron Letters, 2006, vol. 47, # 43, p. 7551 - 7556
[2] Patent: US7045545, 2006, B1. Location in patent: Page/Page column 26
[3] Letters in Organic Chemistry, 2010, vol. 7, # 5, p. 353 - 359
[4] Journal of Medicinal Chemistry, 2008, vol. 51, # 15, p. 4601 - 4608
[5] Patent: WO2014/159224, 2014, A1. Location in patent: Paragraph 00280
