sodium hydrogencarbonate; citric acid in tetrahydrofuran; hexane

1: 95 percent / NaBH4 / dimethylformamide / 3 h / 70 °C 2: 1.) 10percent HCl, 2.) H2 / 1.) methanol, 2.) 20percent Pd(OH)2 / C, 3 atm, 3h View Scheme

sodium tetrahydroborate in N,N-dimethyl-formamide T=70°C; 3 h;