N-iodo-succinimide in trifluorormethanesulfonic acid T=25°C; 2 h;

(i) NaNO2, aq. HCl, (ii) aq. KI; Multistep reaction;

1.1: N-benzyl-N,N,N-triethylammonium chloride; palladium diacetate; sodium hydrogencarbonate / N,N-dimethyl-formamide / 20 h / 45 °C / Inert atmosphere 2.1: R-(+)-proline / water; dimethyl sulfoxide / 0.5 h / 30 °C 3.1: methanol; sodium tetrahydroborate / water; dimethyl sulfoxide / 0.5 h / 0 °C 4.1: palladium 10 on activated carbon; chloroform; hydrogen / ethanol / 12 h 5.1: triethylamine / dichloromethane / 0 °C / Inert atmosphere 5.2: 15 h / 20 °C / Inert atmosphere 6.1: N,N-dimethyl-formamide / 19 h / 75 °C / Inert atmosphere 7.1: dihydrogen peroxide; sodium hydroxide / water / 3 h / 100 °C 7.2: pH Ca. 1 View Scheme

copper T=200°C;