1.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 1 h / 50 °C 1.2: 3.5 h / 50 °C / Reflux 2.1: hydrogen / palladium 10 on activated carbon / methanol / 1 h / 40 °C / 750.08 Torr 3.1: water; acetone / 3.25 h / 20 °C / Reflux 4.1: sodium carbonate / water / pH 8 - 9 View Scheme

1.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 1 h / 50 °C 1.2: 3.5 h / 50 °C / Reflux 2.1: hydrogen / palladium 10 on activated carbon / methanol / 1 h / 40 °C / 750.08 Torr 3.1: water; acetone / 3.25 h / 20 °C / Reflux 4.1: sodium carbonate / water / pH 8 - 9 5.1: sodium carbonate / ethanol; tert-butyl alcohol / 42 h / 50 - 90 °C 6.1: sodium hydroxide; water / methanol / 1.25 h / 20 °C / cooling with ice View Scheme

1: With pyridine; hydroxylamine hydrochloride in tetrahydrofuran T=50°C; 1 h; 2: With acetic anhydride in tetrahydrofuran T=50°C; 3.5 h; Reflux;

1.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 1 h / 50 °C 1.2: 3.5 h / 50 °C / Reflux 2.1: hydrogen / palladium 10 on activated carbon / methanol / 1 h / 40 °C / 750.08 Torr 3.1: water; acetone / 3.25 h / 20 °C / Reflux 4.1: sodium carbonate / water / pH 8 - 9 5.1: sodium carbonate / ethanol; tert-butyl alcohol / 42 h / 50 - 90 °C 6.1: sodium hydroxide; water / methanol / 1.25 h / 20 °C / cooling with ice 7.1: sodium hydroxide; dihydrogen peroxide / water; dimethyl sulfoxide / 2.25 h / 20 - 25 °C View Scheme

1.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 2 h / 50 °C 1.2: 2 h / 80 °C 2.1: platinum on carbon; hydrogen / ethyl acetate / 25 - 30 °C / 6000.6 - 7500.75 Torr / |Autoclave 3.1: acetone; water / 25 - 65 °C / |Resolution of racemate View Scheme

Stage #1: <a href="#" onclick="return RXDsubstances(event, this, '605365', constants.ctx, '0')">N,N-dimethyl-formamide</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '956581', constants.ctx, '0')">trichlorophosphate</a> <br />T=0&deg;C;&nbsp;Vilsmeier-Haack Formylation;&nbsp;1&nbsp;h;&nbsp;&nbsp;Inert atmosphere;&nbsp;<br />Stage #2: <a href="#" onclick="return RXDsubstances(event, this, '21898867', constants.ctx, '0')">1-(3-benzoyloxypropyl)-5-(2-nitropropyl)-2,3-dihydroindole</a> T=0 - 80&deg;C;&nbsp;Vilsmeier-Haack Formylation;&nbsp;2&nbsp;h;&nbsp;&nbsp;Inert atmosphere;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1.1: trichlorophosphate / 0.67 h / cooling with ice<br />1.2: 3 h / 20 &deg;C<br />1.3: 0.5 h<br />2.1: ammonium acetate / 1 h / Reflux<br />3.1: ethanol; sodium tetrahydroborate / tetrahydrofuran / 1.5 h / 20 &deg;C / cooling with ice<br />3.2: 1 h / pH 4<br />4.1: trichlorophosphate / 0.83 h / cooling with ice<br />4.2: 2.58 h / 50 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1.1: ethanol; sodium tetrahydroborate / tetrahydrofuran / 1.5 h / 20 &deg;C / cooling with ice<br />1.2: 1 h / pH 4<br />2.1: trichlorophosphate / 0.83 h / cooling with ice<br />2.2: 2.58 h / 50 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1.1: triethylamine / N,N-dimethyl-formamide / 20 - 50 &deg;C<br />1.2: 6 h / 100 &deg;C<br />2.1: trichlorophosphate / 0.67 h / cooling with ice<br />2.2: 3 h / 20 &deg;C<br />2.3: 0.5 h<br />3.1: ammonium acetate / 1 h / Reflux<br />4.1: ethanol; sodium tetrahydroborate / tetrahydrofuran / 1.5 h / 20 &deg;C / cooling with ice<br />4.2: 1 h / pH 4<br />5.1: trichlorophosphate / 0.83 h / cooling with ice<br />5.2: 2.58 h / 50 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1.1: ammonium acetate / 1 h / Reflux<br />2.1: ethanol; sodium tetrahydroborate / tetrahydrofuran / 1.5 h / 20 &deg;C / cooling with ice<br />2.2: 1 h / pH 4<br />3.1: trichlorophosphate / 0.83 h / cooling with ice<br />3.2: 2.58 h / 50 &deg;C<br /> <br /> &nbsp;