Reagents and conditions: (a)
N2H4·H2O, EtOH, room temperature
(rt); (b) i. di-tert-butylcarbazate, PPh3, THF, 0 °C; ii. HCl in dioxane, rt; (c) (E)-ethyl 2-cyano-3-ethoxyacrylate 5, EtOH, 80 °C;
(d) CH3I, NaH, DMF, 0 °C to rt; (e) i. NaOH, EtOH/H2O, reflux; ii. AcOH, reflux; (f) BH3·Me2S, THF, rt.