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X. Feng et al.
residue, which was purified by silica gel flash chromatog-
raphy with ether–ethyl acetate 8:1 (Rf = 0.4) to give alkene
10b in E/Z mixture. To a solution of the mixture in 20 cm3
methanol was added 0.2 g 10% Pd/C. The reaction mixture
was hydrogenated for 3 h at room temperature. The
mixture was then filtered. The filtrate was concentrated to
give compound 11 as a colorless oil (1.4 g, 76% from 9).
1H NMR (500 MHz, CDCl3): d = 0.86 (t, J = 7 Hz, 3H),
1.24–1.28 (m, 10H), 1.40 (s, 3H), 1.42 (s, 3H), 1.55–1.62
(m, 4H), 2.41 (s, 2H), 2.54 (t, J = 8 Hz, 2H), 2.60–2.63
(m, 2H), 3.47 (d, J = 11 Hz, 2H), 3.77 (d, J = 12 Hz, 2H),
7.01–7.14 (m, 4H) ppm; 13C NMR (100 MHz, CDCl3):
d = 14.0, 22.6, 27.3, 28.2, 29.2, 29.3, 29.4, 29.6, 31.5,
31.8, 35.5, 37.5, 48.7, 65.9, 69.9, 98.2, 128.0, 128.4, 138.9,
140.5 ppm; HRMS-FAB: m/z calcd. for C22H39NO2 [M]?
347.2824, found 347.2825.
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2-Amino-2-[2-(4-octylphenyl)ethyl]-1,3-propandiol,
hydrochloride (FTY720, 1)
A solution of 0.7 g 11 (2.1 mmol) in 2 cm3 methanol and
2.5 cm3 aqueous HCl (1 M) was heated at 50 °C for 3 h.
The solvent was then evaporated to dryness to give crude
compound 1, which was crystallized from CH2Cl2–MeOH
(15:1) to give pure FTY720 (0.5 g, 81%). M.p.:
103–105 °C ([8] 105 °C).
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Acknowledgments We gratefully acknowledge financial support
for new century excellent talents in university (NCET). We also thank
Laboratory of Organic Functional Molecules, the Sino–French Insti-
tute of ECNU for support.
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