sodium methylate in methanol 1 h; Ambient temperature;

1: 89.9 percent / NaOH / diethyl ether / 4 h / Ambient temperature 2: 93 percent / NaN3, NH4Cl / ethanol; H2O / 2 h / Heating 3: 48.6 percent / lipase PS-on-Celite (Pseudomonas sp., Amano), t-BuOMe / 55 h / Ambient temperature 4: 97.2 percent / K2CO3 / methanol / 2.5 h / Ambient temperature 5: 80.8 percent / Ph3P, diethyl azidocarboxylate / tetrahydrofuran / 2.5 h / Ambient temperature 6: 96.7 percent / NaOMe / methanol / 1 h / Ambient temperature View Scheme

1: 93 percent / NaN3, NH4Cl / ethanol; H2O / 2 h / Heating 2: 48.6 percent / lipase PS-on-Celite (Pseudomonas sp., Amano), t-BuOMe / 55 h / Ambient temperature 3: 97.2 percent / K2CO3 / methanol / 2.5 h / Ambient temperature 4: 80.8 percent / Ph3P, diethyl azidocarboxylate / tetrahydrofuran / 2.5 h / Ambient temperature 5: 96.7 percent / NaOMe / methanol / 1 h / Ambient temperature View Scheme

1: 82.3 percent / N-bromosuccinimide / tetrahydrofuran; H2O / 12 h / Ambient temperature 2: 89.9 percent / NaOH / diethyl ether / 4 h / Ambient temperature 3: 93 percent / NaN3, NH4Cl / ethanol; H2O / 2 h / Heating 4: 48.6 percent / lipase PS-on-Celite (Pseudomonas sp., Amano), t-BuOMe / 55 h / Ambient temperature 5: 97.2 percent / K2CO3 / methanol / 2.5 h / Ambient temperature 6: 80.8 percent / Ph3P, diethyl azidocarboxylate / tetrahydrofuran / 2.5 h / Ambient temperature 7: 96.7 percent / NaOMe / methanol / 1 h / Ambient temperature View Scheme

1: 80.8 percent / Ph3P, diethyl azidocarboxylate / tetrahydrofuran / 2.5 h / Ambient temperature 2: 96.7 percent / NaOMe / methanol / 1 h / Ambient temperature View Scheme

1: 97.2 percent / K2CO3 / methanol / 2.5 h / Ambient temperature 2: 80.8 percent / Ph3P, diethyl azidocarboxylate / tetrahydrofuran / 2.5 h / Ambient temperature 3: 96.7 percent / NaOMe / methanol / 1 h / Ambient temperature View Scheme