L-(+)-tartaric acid

lithium aluminium tetrahydride; diethyl ether

Irradiationmild conditions;

hydrolysis;

1: 93 percent / xylene / 2 h / Heating 2: 1.) SOCl2, 2.) LiBr / 1.) CHCl3, 8 h, 2.) Me2CO, 6 h 3: 80 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 4: 73 percent / NH2NH2*H2O / acetonitrile / 4 h / Heating View Scheme

1: CH2Cl2 / 6 h / 0 °C 2: (i) NaH, THF, (ii) /BRN= 969135/ 3: aq. HCl / Heating View Scheme

1: 93 percent / xylene / 2 h / Heating 2: 85 percent / ZnCl2 / benzene / 12 h / Heating 3: 70 percent / NBS, CaCl2 / benzene / 0.33 h / Irradiation 4: Raney Ni W2 / ethanol / 6 h 5: 90 percent / NH2NH2*H2O / acetonitrile / 6 h / Heating 6: 10 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 7: 98 percent / K2CO3 / acetonitrile / 2 h / Heating 8: 90 percent / ammonium formate / Pd/C / 1 h / Heating View Scheme

1: CH2Cl2 / 6 h / 0 °C 2: (i) NaH, THF, (ii) /BRN= 969135/ View Scheme

in benzene 16 h; Heating;

1: NaOMe / methanol / 3.5 h / 20 °C 2: (+/-)-10-camphorsulfonic acid / acetone / 4 h / 20 °C 3: H2NNH2*H2O / 2.5 h / Heating View Scheme