palladium 10 on activated carbon; hydrogen in methanol; ethyl acetate T=20°C; 24 h; Inert atmosphere;

1: sodium bis(2-methoxyethoxy)aluminium dihydride / ethylene glycol dimethyl ether; toluene / 3 h / 0 - 25 °C / Inert atmosphere 2: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 20 h / 25 °C / Inert atmosphere 3: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 4 h / 25 °C / Inert atmosphere 4: hydrazine hydrate / ethanol / 3 h / Reflux View Scheme

1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 20 h / 25 °C / Inert atmosphere 2: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 4 h / 25 °C / Inert atmosphere 3: hydrazine hydrate / ethanol / 3 h / Reflux View Scheme

1: titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate / N-undecane; dichloromethane / 3.5 h / -20 °C / Molecular sieve 2: sodium bis(2-methoxyethoxy)aluminium dihydride / ethylene glycol dimethyl ether; toluene / 3 h / 0 - 25 °C / Inert atmosphere 3: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 20 h / 25 °C / Inert atmosphere 4: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 4 h / 25 °C / Inert atmosphere 5: hydrazine hydrate / ethanol / 3 h / Reflux View Scheme

1.1: BH3*N,N-diethylanilline; (R)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c]-[1,3,2]oxazaborole / toluene / 6 h / 20 °C / Inert atmosphere 1.2: 0.17 h / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 3 h / 20 °C / Inert atmosphere 3.1: sodium carbonate / hexane / 6 h / 0 °C / Inert atmosphere 3.2: 12 h / 20 °C / Inert atmosphere 4.1: caesium carbonate / tetrahydrofuran; N,N-dimethyl-formamide / 20 h / 60 °C / Inert atmosphere 5.1: palladium 10 on activated carbon; hydrogen / methanol; ethyl acetate / 24 h / 20 °C / Inert atmosphere View Scheme

1.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 3 h / 20 °C / Inert atmosphere 2.1: sodium carbonate / hexane / 6 h / 0 °C / Inert atmosphere 2.2: 12 h / 20 °C / Inert atmosphere 3.1: caesium carbonate / tetrahydrofuran; N,N-dimethyl-formamide / 20 h / 60 °C / Inert atmosphere 4.1: palladium 10 on activated carbon; hydrogen / methanol; ethyl acetate / 24 h / 20 °C / Inert atmosphere View Scheme