N-Boc-d/L-alaninol

Chemical Properties

Off-white Solid

Uses

N-BOC-D/L-ALANINOL is used in the preparation of heterocyclic compounds, as integrase inhibiting antiviral agents.

Synthesis Reference(s)

The Journal of Organic Chemistry, 46, p. 4799, 1981 DOI: 10.1021/jo00336a040

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. Under stirring, 30 g (133 mmol) of di-tert-butyl dicarbonate was added to the solution in one go. The reaction mixture was stirred continuously 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 obtained was dissolved in 300 mL of ethyl acetate. It was washed twice sequentially with 200 ml of water and then once with 200 ml of saturated aqueous sodium chloride solution. The organic phase was dried with magnesium sulfate 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): δ 4.71 (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