1: 72 percent / H2 / RaNi / methanol / 2.5 h 2: 99 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 3: 78 percent / NaBH3CN / acetonitrile; H2O / 1 h / Ambient temperature View Scheme

<b>Multi-step reaction with 4 steps<br /> </b>1: 81 percent / PdCl₂(PhCN)2, CuI, piperidine / tetrahydrofuran / 18 h / Ambient temperature<br />2: 95 percent / H₂, quinoline / Linlar catralyst / methanol; CH₂Cl₂ / 0.67 h<br />3: 91 g / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, DMAP, TEMPO / CH₂Cl₂ / 3.5 h / Ambient temperature<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 95 percent / H₂, quinoline / Linlar catralyst / methanol; CH₂Cl₂ / 0.67 h<br />2: 91 g / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, DMAP, TEMPO / CH₂Cl₂ / 3.5 h / Ambient temperature<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 84 g / aq. NaOH / ethanol / 2.5 h / Heating<br />2: 91 g / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, DMAP, TEMPO / CH₂Cl₂ / 3.5 h / Ambient temperature<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: 96 percent / 10percent aq. NaOH<br />2: 1.) sec-BuLi, 2.) TMEDA / 1.) -78 deg C<br />3: 50 percent / CrCl₂ / tetrahydrofuran<br />4: 81 percent / PdCl₂(PhCN)2, piperidine, CuI / tetrahydrofuran / Ambient temperature<br />5: 1.) H₂, quinoline, 2.) DEAC, DMAP, TEMPO, 3.) TEMPO, 4.) DBU, 5.) (Boc)2O, aq. NaOH / 1.) Lindlar catalyst<br /> <br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>1: aq. NaOH<br />2: 1.) sec-BuLi, TMEDA / 1.) Et₂O, cyclohexane, -72 to -20 deg C, 15 min, -20 deg C, 30 min, 2.) Et₂O, cyclohexane, -72 deg C, 20 min<br />3: 50 percent / CrCl₃ / tetrahydrofuran / 16 h / Ambient temperature<br />4: 81 percent / PdCl₂(PhCN)2, CuI, piperidine / tetrahydrofuran / 18 h / Ambient temperature<br />5: 95 percent / H₂, quinoline / Linlar catralyst / methanol; CH₂Cl₂ / 0.67 h<br />6: 91 g / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, DMAP, TEMPO / CH₂Cl₂ / 3.5 h / Ambient temperature<br /> <br /> &nbsp;