lithium aluminium tetrahydride in diethyl ether 2 h; Heating; Yield given;

1: formic acid With acetic anhydride T=60°C; 1 h; 2: [2-(1H-indol-3-yl)-ethyl]-methyl-amine in dichloromethane T=20°C; 1.5 h;

1: diethyl ether / from 0 deg C up to r.t. 2: LiAlH4 / diethyl ether / 2 h / Heating 3: diethyl ether / from 0 deg C up to r.t. View Scheme

1: LiAlH4 / diethyl ether / 2 h / Heating 2: diethyl ether / from 0 deg C up to r.t. View Scheme

in diethyl ether from 0 deg C up to r.t.;

1.1: t-BuOCl; triethylamine / tetrahydrofuran / 0.5 h / -78 °C 1.2: tetrahydrofuran / 1.5 h / -78 - 20 °C 1.3: H2O2; NaOH / tetrahydrofuran; H2O / 1 h / 20 °C 2.1: 61 percent / N-bromosuccinimide; acetic acid; formic acid / 0.5 h / 20 °C 3.1: NaOH / ethanol / 24 h / Heating View Scheme