sodium methylate in methanol

1: 85 percent / pyridine / 0 deg C -> r.t., overnight 2: 30 percent / tributyltin methoxide / tetrahydrofuran / Heating 3: 86 percent / pyridine 4: 56 percent / NaN3 / dimethylsulfoxide / 80 deg C, 1 h; 60 deg C, overnight 5: 81 percent / H2 / 5percent Pd/C / toluene / 24 h 6: 101 percent / pyridine / Ambient temperature 7: 100 percent / NaOMe / methanol View Scheme

1: 30 percent / tributyltin methoxide / tetrahydrofuran / Heating 2: 86 percent / pyridine 3: 56 percent / NaN3 / dimethylsulfoxide / 80 deg C, 1 h; 60 deg C, overnight 4: 81 percent / H2 / 5percent Pd/C / toluene / 24 h 5: 101 percent / pyridine / Ambient temperature 6: 100 percent / NaOMe / methanol View Scheme

1: 76 percent / pyridine / Ambient temperature 2: 73 percent / H2 / 5percent Pd/C / ethyl acetate; ethanol / 3102.9 Torr 3: 86 percent / pyridine 4: 56 percent / NaN3 / dimethylsulfoxide / 80 deg C, 1 h; 60 deg C, overnight 5: 81 percent / H2 / 5percent Pd/C / toluene / 24 h 6: 101 percent / pyridine / Ambient temperature 7: 100 percent / NaOMe / methanol View Scheme

1: 86 percent / pyridine 2: 56 percent / NaN3 / dimethylsulfoxide / 80 deg C, 1 h; 60 deg C, overnight 3: 81 percent / H2 / 5percent Pd/C / toluene / 24 h 4: 101 percent / pyridine / Ambient temperature 5: 100 percent / NaOMe / methanol View Scheme

1: 84 percent / Et3N 2: 1) HCl, 2) pyridine / 1) MeOH 3: 91 percent / cyclohexene / 10percent Pd-C / methanol 4: NEt3 5: NaI / ethyl acetate 6: NaN3 / dimethylformamide 7: NaOMe / methanol 8: H2 / 10percent Pd-C 9: acetone; H2O View Scheme

1: NEt3 2: NaI / ethyl acetate 3: NaN3 / dimethylformamide 4: NaOMe / methanol 5: H2 / 10percent Pd-C 6: acetone; H2O View Scheme

1: 1) HCl, 2) pyridine / 1) MeOH 2: 91 percent / cyclohexene / 10percent Pd-C / methanol 3: NEt3 4: NaI / ethyl acetate 5: NaN3 / dimethylformamide 6: NaOMe / methanol 7: H2 / 10percent Pd-C 8: acetone; H2O View Scheme

in water; acetone Yield given;