N-methyl-2-indolinone; tetrapropylammonium perruthennate in dichloromethane T=20°C; Oxidation; 0.416667 h;

1: H2, Wilkinson catalyst 2: O3 / ethanol / -78 °C 3: NaBH4 / tetrahydrofuran; ethanol 4: imidazole / dimethylformamide 5: Br2 / CCl4 6: 67 percent / Li2CO3, LiBr / dimethylformamide 7: tetrahydrofuran 8: LiN(iPr)2 / tetrahydrofuran 9: LiCl, methanesulfonyl chloride / dimethylformamide 10: K2CO3, CuI, Bu4NBr / dimethylformamide 11: 90 percent / H2 / Lindlar catalyst 12: 83 percent / Bu4NF, H2O / tetrahydrofuran 13: Dess-Martin periodinane, NaOAc / CH2Cl2 14: TiCl3*DME1.5, Zn-Cu / 1,2-dimethoxy-ethane / 36 h / 0 °C 15: 1.) MsCl, pyridine 2.) Bu4NOH / 1.) ether; 2.) THF 16: LiN(iPr)2 / tetrahydrofuran 17: 84 percent / Dess-Martin periodinane View Scheme

1: NaBH4 / tetrahydrofuran; ethanol 2: imidazole / dimethylformamide 3: Br2 / CCl4 4: 67 percent / Li2CO3, LiBr / dimethylformamide 5: tetrahydrofuran 6: LiN(iPr)2 / tetrahydrofuran 7: LiCl, methanesulfonyl chloride / dimethylformamide 8: K2CO3, CuI, Bu4NBr / dimethylformamide 9: 90 percent / H2 / Lindlar catalyst 10: 83 percent / Bu4NF, H2O / tetrahydrofuran 11: Dess-Martin periodinane, NaOAc / CH2Cl2 12: TiCl3*DME1.5, Zn-Cu / 1,2-dimethoxy-ethane / 36 h / 0 °C 13: 1.) MsCl, pyridine 2.) Bu4NOH / 1.) ether; 2.) THF 14: LiN(iPr)2 / tetrahydrofuran 15: 84 percent / Dess-Martin periodinane View Scheme

1: O3 / ethanol / -78 °C 2: NaBH4 / tetrahydrofuran; ethanol 3: imidazole / dimethylformamide 4: Br2 / CCl4 5: 67 percent / Li2CO3, LiBr / dimethylformamide 6: tetrahydrofuran 7: LiN(iPr)2 / tetrahydrofuran 8: LiCl, methanesulfonyl chloride / dimethylformamide 9: K2CO3, CuI, Bu4NBr / dimethylformamide 10: 90 percent / H2 / Lindlar catalyst 11: 83 percent / Bu4NF, H2O / tetrahydrofuran 12: Dess-Martin periodinane, NaOAc / CH2Cl2 13: TiCl3*DME1.5, Zn-Cu / 1,2-dimethoxy-ethane / 36 h / 0 °C 14: 1.) MsCl, pyridine 2.) Bu4NOH / 1.) ether; 2.) THF 15: LiN(iPr)2 / tetrahydrofuran 16: 84 percent / Dess-Martin periodinane View Scheme

1: Br2 / CCl4 2: 67 percent / Li2CO3, LiBr / dimethylformamide 3: tetrahydrofuran 4: LiN(iPr)2 / tetrahydrofuran 5: LiCl, methanesulfonyl chloride / dimethylformamide 6: K2CO3, CuI, Bu4NBr / dimethylformamide 7: 90 percent / H2 / Lindlar catalyst 8: 83 percent / Bu4NF, H2O / tetrahydrofuran 9: Dess-Martin periodinane, NaOAc / CH2Cl2 10: TiCl3*DME1.5, Zn-Cu / 1,2-dimethoxy-ethane / 36 h / 0 °C 11: 1.) MsCl, pyridine 2.) Bu4NOH / 1.) ether; 2.) THF 12: LiN(iPr)2 / tetrahydrofuran 13: 84 percent / Dess-Martin periodinane View Scheme

1: tetrahydrofuran 2: LiN(iPr)2 / tetrahydrofuran 3: LiCl, methanesulfonyl chloride / dimethylformamide 4: K2CO3, CuI, Bu4NBr / dimethylformamide 5: 90 percent / H2 / Lindlar catalyst 6: 83 percent / Bu4NF, H2O / tetrahydrofuran 7: Dess-Martin periodinane, NaOAc / CH2Cl2 8: TiCl3*DME1.5, Zn-Cu / 1,2-dimethoxy-ethane / 36 h / 0 °C 9: 1.) MsCl, pyridine 2.) Bu4NOH / 1.) ether; 2.) THF 10: LiN(iPr)2 / tetrahydrofuran 11: 84 percent / Dess-Martin periodinane View Scheme

1: 1.) MCPBA, 2.) LDA 2: 21 percent / TBHP, SeO2 3: 90 percent / DMAP, pyridine / Ambient temperature 5: 11 percent / BuLi, TMEDA / hexane / 10 h / Ambient temperature 6: 43 percent / MnO2 / benzene / 3 h / Heating View Scheme

1: 21 percent / TBHP, SeO2 2: 90 percent / DMAP, pyridine / Ambient temperature 4: 11 percent / BuLi, TMEDA / hexane / 10 h / Ambient temperature 5: 43 percent / MnO2 / benzene / 3 h / Heating View Scheme

1: TiCl3*DME1.5, Zn-Cu / 1,2-dimethoxy-ethane / 36 h / 0 °C 2: 1.) MsCl, pyridine 2.) Bu4NOH / 1.) ether; 2.) THF 3: LiN(iPr)2 / tetrahydrofuran 4: 84 percent / Dess-Martin periodinane View Scheme

1: LiN(iPr)2 / tetrahydrofuran 2: 84 percent / Dess-Martin periodinane View Scheme