sodium tetrahydroborate; nickel in methanol; water T=20°C;

1: 1.) LDA / 1.) THF, hexane, -60 deg C, 30 min, 2.) THF, hexane, a) -78 deg C, 1 h, b) RT, overnight 2: 1.) TFA, 2.) 0.75 N HCl, AcOH, wet Dowex 50W X8 / 1.) CH2Cl2, from 0 deg C to RT, overnight, 2.) toluene, 100 deg C, 20 h View Scheme

hydrogen bromide

1: ethanol 2: aqueous HBr View Scheme