Chemical Properties
Colorless to yellow liquid or low melting solid
Uses
(R)-(+)-2-Amino-3-benzyloxy-1-propanol is used as a reagent to synthesize beta-amino alcohols, compounds that are used as therapeutic agents to treat heart disease. (R)-(+)-2-Amino-3-benzyloxy-1-propanol is also used as a reagent to synthesize 15-membered macrolide antibiotics, drugs that are used to treat respiratory tract infections.
Synthesis
General procedure for the synthesis of O-benzyl-L-serinol from (S)-2-amino-3-(benzyloxy)propionic acid: O-benzyl-L-serine (15.0 g, 76.8 mmol) was slowly added to a tetrahydrofuran (THF, 150 mL) suspension of lithium aluminum hydride (4.37 g, 115.3 mmol) under reflux conditions. The reaction mixture was stirred at reflux temperature for 1.5 h. After cooling in an ice bath, distilled water (4.4 mL), 10% NaOH aqueous solution (4.4 mL), and distilled water (4.4 mL) were added sequentially. After stirring for 18 h at room temperature, the mixture was filtered and the filter cake was washed with THF. The filtrate was concentrated under reduced pressure to remove the solvent, and the residue was purified by silica gel column chromatography (eluent ratio CHCl3/MeOH/NH4OH = 10:1:0.1) to afford the target product, O-benzyl-L-serinol (6.43 g, 69% yield), as a colorless foamy substance. Its physical properties were as follows: [α]27D -5.0 (c 0.760, methanol); 1H NMR (CDCl3) δ 7.27-7.41 (m, 5H), 4.53 (s, 2H), 3.39-3.67 (m, 4H), 3.03-3.17 (m, 1H), 1.85 (br s, 3H); 13C NMR (CDCl3) δ 137.9, 128.2, 127.55, 127.50, 73.1, 72.5, 63.7, 52.3; MS (ESI) m/z 182.2 [M + H]+. The NMR data are in agreement with literature reports.
References
[1] Liebigs Annalen der Chemie, 1988, p. 851 - 854
[2] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 19, p. 5787 - 5801
[3] Tetrahedron, 2002, vol. 58, # 46, p. 9387 - 9401
[4] Tetrahedron, 1975, vol. 31, p. 2629 - 2632
[5] Molecules, 2009, vol. 14, # 12, p. 5124 - 5143
