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Reagents and conditions: (a) concentrated HCl, NaNO2, H2O, 0 °C, 15 min; (b) NaN3, H2O, room temperature, 2 h; (c) MeONa, 1-((4-(tert-butyl)phenyl)sulfonyl)propan-2-one, MeOH, 60 °C, overnight; (d) Pd(Ph3P)4, ZnCN, DMF, 90 °C, overnight; (e) CO(50 psi), Pd(dppf)2Cl2, MeOH, 80 °C, 16 h; (f) LiBH4, THF; (g) NH3, MeOH; (h) tributyl(1-ethoxyvinyl)stannane, Pd(PPh3)2Cl2, dioxane; (i) supercritical fluid chromatography (SFC).
