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Reagents and conditions:
(a) HCl, MeOH, 89% (b) conc. HCl, reflux in sealed tube, 6 h, 77% (c) tBuNH2, py, DMF, 80 °C, 80% (d) ethyl acrylate, K2CO3, Pd(OAc)2, dppp, DMF, MW, 130 °C, 7 h, 81% (e) DIBALH, CH2Cl2, −78 °C, 74% (f) NaNO2, AcOH, 57% (crude) (g) TBSONHTs, DEAD, PPh3, THF, 62% (h) CsF, MeCN, 48% (i) SOCl2, 0 °C, DMF, 99% and (j) 4.0 M HCl in dioxane, 99%.
