morpholine; sodium bis(2-methoxyethoxy)aluminium dihydride in toluene T=-10°C; 2 h;

1.1: NaH / dimethylformamide / 1 h / 20 °C 1.2: NaI / dimethylformamide / 14 h / 80 °C 2.1: 25.1 g / NaH / dimethylformamide / 15 h / 80 °C 3.1: 21 percent / H2SO4; AcOH / 2.5 h / 90 °C 4.1: DMAP / tetrahydrofuran / 1.5 h / Heating View Scheme

1.1: NaH / dimethylformamide / 1 h / 20 °C 1.2: NaI / dimethylformamide / 14 h / 80 °C 2.1: 25.1 g / NaH / dimethylformamide / 15 h / 80 °C 3.1: 21 percent / H2SO4; AcOH / 2.5 h / 90 °C 4.1: DMAP / tetrahydrofuran / 1.5 h / Heating 5.1: 3.89 g / sodium methoxide / 2.5 h / Heating 6.1: NaBH4 / tetrahydrofuran; methanol / 1 h / -15 °C 7.1: Et3N / tetrahydrofuran / 14 h / 20 °C 8.1: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 9.1: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C View Scheme

1.1: NaH / dimethylformamide / 1 h / 20 °C 1.2: NaI / dimethylformamide / 14 h / 80 °C 2.1: 25.1 g / NaH / dimethylformamide / 15 h / 80 °C 3.1: 21 percent / H2SO4; AcOH / 2.5 h / 90 °C View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '103233', constants.ctx, '0')">pyridine</a> <br />T=20&deg;C;&nbsp;40&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: pyridine / tetrahydrofuran / 14.5 h / 20 &deg;C<br />2: bromine; sodium acetate / water; acetic acid / 2 h / 70 &deg;C<br /> <br /> &nbsp;