@article{870edc1665fa441bb199127ee80f4c43,
title = "A convenient synthesis of (2S)-2-Amino-3-phenylpropanol",
author = "Ramalinga Dharanipragada and Arled Alarcon and Hruby, \{Victor J.\}",
note = "Funding Information: --\textasciitilde{}0-3-phenV\textasciitilde{}DrODan.-O T{\~o} a two liter, three-necked round bottom flask, equipped with a mechanical stirrer, reflux condenser and addition funnel, 600 mL (1.2 mole, 2 eq) of LiBH, (2 M solution in TI-IF) was transferred a doubleended needle. To this stirred solution, 304 mL (2.4 moles, 4 eq) of chlorotrimethylsilane was added dropwise over 1.5 hr under an atmosphere of argon. A total of 100 g (0.6 mole, 1 eq) of L-phenylalanine (1) was added in small portions over a period of 4 hrs by means of a powder funnel. The reaction mixhut was stirred at ambient temperature for 24 hrs. At the end of this time, the reaction was quenched by the careful addition of 600 mL of methanol, followed by 450 mL of 20\% potassium hydroxide solution. After removal of methanol irr m,6 00 mL of water was added. The solution was extracted with chloroform (3 x 300 mL), washed once with 50 mL of water, dried (Na,SO,) and filtered. Removal of solvent in ucu! left 95 g of a colorless solid. Recrystallization from 190 mL of ethyl acetate gave 75 g. (83\%) of pure L-phenylalaninol(2), mp. 85-86{"}, lit.2 mp. 88.5-91{"}, [a]:=- 23.5{"} (c 1.0, EtOH), lit.2 [a]:=- 24.7' (c 1.0, EtOH). CIMS: m/e = =152 (M++1,100\%); 'H NMR (250 MHz, CDCl,): 6 1.98 (br s, 3H, -OH), 2.52 (dd, J = 13.4, 8.6 Hz, lH, HCH C,H,), 2.79 (dd, J = 13.4, 5.1 Hz, lH, HCHC,H,), 3.06-3.15 (m, lH, CI-lNI-\$),3 .39 (dd, J = 10.6,7.3 Hz, lH, HCHOH), 3.64 (dd, J = 10.7,3.8 Hz, lH, HCHOH), 7.17-7.34 (m, 5H, Arm. IR (solution in C\&ClJ: 3620,3039,3010,2927, 1494, 1453, 1035 cm-'. u.C alcd. forC,H,,NO: C, 71.48; H, 8.66. Found: C, 71.75; H, 8.85 Acknow1edeements.-We thank the U. S. Public Health Service for fmancial support. Arled Alarcon was a part of the UA Undergraduate Biology Research Program, supported in part by an NSF REU grant (DIR 8900796) and in part by the U. S. Public Health Service.",
year = "1991",
month = jun,
doi = "10.1080/00304949109458222",
language = "English (US)",
volume = "23",
pages = "396--397",
journal = "Organic Preparations and Procedures International",
issn = "0030-4948",
publisher = "Taylor and Francis Ltd.",
number = "3",
}