sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate in dichloromethane T=20°C; 3 h;

1: 20 percent / silver trifluoromethanesulfonate, sym-collidine, 4 Angstroem molecular sieves / CH2Cl2 / Ambient temperature 2: 1.) H2 / 1.) 5percent palladium-on-charcoal / 1.) aq. EtOH, 3h, room temperature; 2.) methanol, 6h View Scheme

1: 20 percent / silver trifluoromethanesulfonate, sym-collidine, 4 Angstroem molecular sieves / CH2Cl2 / Ambient temperature 2: 1.) H2 / 1.) 5percent palladium-on-charcoal / 1.) aq. EtOH, 3h, room temperature; 2.) methanol, 6h View Scheme

1: 10 percent / silver trifluoromethanesulfonate, sym-collidine, 4 Angstroem molecular sieves / CH2Cl2 / Ambient temperature 2: 1.) H2 / 1.) 5percent palladium-on-charcoal / 1.) aq. EtOH, 3h, room temperature; 2.) methanol, 6h View Scheme

1: 1.) azidonitration; 2.) oxalyl chloride / 2.) CH2Cl2, DMF, 1h, 0 deg C 2: 10 percent / silver trifluoromethanesulfonate, sym-collidine, 4 Angstroem molecular sieves / CH2Cl2 / Ambient temperature 3: 1.) H2 / 1.) 5percent palladium-on-charcoal / 1.) aq. EtOH, 3h, room temperature; 2.) methanol, 6h View Scheme

hydrogen; palladium on activated charcoal 1.) aq. EtOH, 3h, room temperature; 2.) methanol, 6h; Yield given. Multistep reaction;

methanol; sodium methylate T=20°C; 1 h;