1.1: sodium tetrahydroborate / water; acetonitrile / 0.17 h / 25 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C 2.2: 18 h / 20 °C 3.1: C19H23BNO3(1-)*H(1+); borane-THF / 1,4-dioxane; tetrahydrofuran / 0 °C / |Inert atmosphere View Scheme

1.1: sodium tetrahydroborate / water; acetonitrile / 0.17 h / 25 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C 2.2: 18 h / 20 °C 3.1: C19H23BNO3(1-)*H(1+); borane-THF / 1,4-dioxane; tetrahydrofuran / 0 °C / |Inert atmosphere View Scheme

dodecacarbonyltriiron in 1,2-dichloro-ethane 1.) r.t., 4 h; 2.) 80 deg C, 20 h; Yields of byproduct given;

in methanol T=20°C; 0.5 h;

1: (i) TsOH, (ii) /BRN= 610776/, Et2O 2: aq. HBr / CHCl3 3: Et3N / methanol View Scheme