1: 98 percent / NaOMe / methanol 2: 94 percent / pyridine 3: 100 percent / NaN3 / dimethylformamide / 80 °C 4: 86 percent / NaH / dimethylformamide 5: N-iodosuccinimide; silver trifluoromethanesulfonate / diethyl ether; CH2Cl2 / -20 °C 6: NaOMe / methanol 7: P(CH3)3; 0.1 N aq. NaOH / tetrahydrofuran 8: H2; aq. AcOH / 20 percent Pd(OH)2/C View Scheme

sodium methylate in methanol 5 h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;