M. Adamczyk et al. / Tetrahedron: Asymmetry 11 (2000) 2289±2298
2297
3.7. (+)-Deoxypyridinoline (Dpd 1c)
The reaction of (S)-(^)-amine 2c (0.060 g, 0.198 mmol) and (S)-(^)-bromide 5 (0.190 g, 0.396
mmol, 2.0 equiv.) was carried out by following the procedure described for (+)-Pyd 1b. The
residue was dissolved in 0.1% TFA±MeCN:0.1% TFA±H2O (20 mL, 1:99 ratio). The crude
product was puri®ed by preparative reversed phase HPLC [Waters, C18, RCM, mBondpak, 10.0
mm, 3Â(40Â100 mm), using 0.1% TFA±MeCN:0.1% TFA±H2O, 1:99, 20 mL/min at 215 nm].
Concentration of the product to about 120 mL volume, and lyophilization aorded 0.072 g of
(+)-Dpd 1c as its TFA salt in 42% yield.12a Analytical RP HPLC: 0.1% TFA±MeCN:0.1% TFA±
H2O, 1:99, 1.0 mL/min at 215 nm, tR: 4.64 min, 99.7%; ꢁ2D3=+36.2 (c 0.535, MeOH), lit.12a
ꢁ2D3=+31.6 (c 0.25, MeOH); 1H NMR (CD3OD): ꢀ 8.34 (s, 1H), 8.29 (s, 1H), 4.53 (t, 2H, J=6.9
Hz), 4.21 (t, 1H, J=6.9 Hz), 3.97±3.89 (m, 2H), 3.44±3.38 (m, 2H), 3.16±2.92 (m, 2H), 2.36±1.88
(m, 6H), 1.62±1.42 (m, 2H); ESI-MS (m/z): 413 (M)+; HRMS (FAB, m/z): calcd C18H28N4O7:
413.2036 (M)+; observed: 413.2034.
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