lithium aluminium tetrahydride in tetrahydrofuran 18 h; Heating;

1: 1.) n-butyllithium, 2.) 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.) THF, hexane, 2 h, 2.) THF, hexane, -50 deg C -> room temperature 2: 86 percent / pyridinium p-toluene sulfonate / aq. ethanol / 5 h / 53 - 58 °C 3: 97 percent / triethylamine / CH2Cl2 / 0.25 h 4: 70 percent / NaN3 / dimethylsulfoxide 5: triphenylphosphine, boiling stones / tetrahydrofuran; H2O / Ambient temperature 6: LiAlH4 / tetrahydrofuran / 18 h / Heating View Scheme

1: 86 percent / pyridinium p-toluene sulfonate / aq. ethanol / 5 h / 53 - 58 °C 2: 97 percent / triethylamine / CH2Cl2 / 0.25 h 3: 70 percent / NaN3 / dimethylsulfoxide 4: triphenylphosphine, boiling stones / tetrahydrofuran; H2O / Ambient temperature 5: LiAlH4 / tetrahydrofuran / 18 h / Heating View Scheme

1: 97 percent / triethylamine / CH2Cl2 / 0.25 h 2: 70 percent / NaN3 / dimethylsulfoxide 3: triphenylphosphine, boiling stones / tetrahydrofuran; H2O / Ambient temperature 4: LiAlH4 / tetrahydrofuran / 18 h / Heating View Scheme

1: triphenylphosphine, boiling stones / tetrahydrofuran; H2O / Ambient temperature 2: LiAlH4 / tetrahydrofuran / 18 h / Heating View Scheme

1: 70 percent / NaN3 / dimethylsulfoxide 2: triphenylphosphine, boiling stones / tetrahydrofuran; H2O / Ambient temperature 3: LiAlH4 / tetrahydrofuran / 18 h / Heating View Scheme

(i) N2H4*H2O, (ii) NaNH2, liq. NH3; Multistep reaction;

(i) Py, (ii) LiAlH4; Multistep reaction;