hydrogenchloride in methanol 96 h; Ambient temperature;

<b>Multi-step reaction with 5 steps<br /> </b>1: 98 percent / D-Camphor-10-sulfonic acid / benzene / 12 h / Heating<br />2: 84 percent / LiAlH₄ / tetrahydrofuran / 0.25 h / 0 &deg;C<br />3: 83 percent / DMSO, oxalyl chloride, NEt₃ / 1) CH₂Cl₂, -78 deg C, 1 h, 2) 0 deg C, 1 h<br />4: 1) n-butyllithium / 1) THF, hexane, -78 deg C, 4 min, 2) -78 deg C, 30 min<br />5: 72 percent / DMSO, oxalyl chloride, NEt₃ / 1) CH₂Cl₂, -78 deg C, 1 h, 2) 0 deg C, 1 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 8 steps<br /> </b>1: 1) Li, liquid NH₃ / 1) THF, -78 deg C, 45 min, 2) -78 deg C, 30 min<br />2: 1) Hg(OCOCF₃)2, 2) aq. HCl / 1) CH₃NO₂, rt, 42 h, 2) rt, 1 h<br />3: 86 percent / aq. KOH / methanol / 1.5 h / Ambient temperature<br />4: 54 percent / D-camphor-10-sulfonic acid / benzene / 3 h / Heating<br />5: 80 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 &deg;C<br />6: 83 percent / DMSO, oxalyl chloride, NEt₃ / 1) CH₂Cl₂, -78 deg C, 1 h, 2) 0 deg C, 1 h<br />7: 1) n-butyllithium / 1) THF, hexane, -78 deg C, 4 min, 2) -78 deg C, 30 min<br />8: 72 percent / DMSO, oxalyl chloride, NEt₃ / 1) CH₂Cl₂, -78 deg C, 1 h, 2) 0 deg C, 1 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: 54 percent / D-camphor-10-sulfonic acid / benzene / 3 h / Heating<br />2: 80 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 &deg;C<br />3: 83 percent / DMSO, oxalyl chloride, NEt₃ / 1) CH₂Cl₂, -78 deg C, 1 h, 2) 0 deg C, 1 h<br />4: 1) n-butyllithium / 1) THF, hexane, -78 deg C, 4 min, 2) -78 deg C, 30 min<br />5: 72 percent / DMSO, oxalyl chloride, NEt₃ / 1) CH₂Cl₂, -78 deg C, 1 h, 2) 0 deg C, 1 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1: 86 percent / aq. KOH / methanol / 1.5 h / Ambient temperature<br />2: 54 percent / D-camphor-10-sulfonic acid / benzene / 3 h / Heating<br />3: 80 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 &deg;C<br />4: 83 percent / DMSO, oxalyl chloride, NEt₃ / 1) CH₂Cl₂, -78 deg C, 1 h, 2) 0 deg C, 1 h<br />5: 1) n-butyllithium / 1) THF, hexane, -78 deg C, 4 min, 2) -78 deg C, 30 min<br />6: 72 percent / DMSO, oxalyl chloride, NEt₃ / 1) CH₂Cl₂, -78 deg C, 1 h, 2) 0 deg C, 1 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>1: 1) Hg(OCOCF₃)2, 2) aq. HCl / 1) CH₃NO₂, rt, 42 h, 2) rt, 1 h<br />2: 86 percent / aq. KOH / methanol / 1.5 h / Ambient temperature<br />3: 54 percent / D-camphor-10-sulfonic acid / benzene / 3 h / Heating<br />4: 80 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 &deg;C<br />5: 83 percent / DMSO, oxalyl chloride, NEt₃ / 1) CH₂Cl₂, -78 deg C, 1 h, 2) 0 deg C, 1 h<br />6: 1) n-butyllithium / 1) THF, hexane, -78 deg C, 4 min, 2) -78 deg C, 30 min<br />7: 72 percent / DMSO, oxalyl chloride, NEt₃ / 1) CH₂Cl₂, -78 deg C, 1 h, 2) 0 deg C, 1 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>1: 95 percent / pyridinium dichromate / CH₂Cl₂ / 5 h / Ambient temperature<br />2: 98 percent / aq. HCl / methanol / 2 h / Ambient temperature<br />3: 54 percent / D-camphor-10-sulfonic acid / benzene / 3 h / Heating<br />4: 80 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 &deg;C<br />5: 83 percent / DMSO, oxalyl chloride, NEt₃ / 1) CH₂Cl₂, -78 deg C, 1 h, 2) 0 deg C, 1 h<br />6: 1) n-butyllithium / 1) THF, hexane, -78 deg C, 4 min, 2) -78 deg C, 30 min<br />7: 72 percent / DMSO, oxalyl chloride, NEt₃ / 1) CH₂Cl₂, -78 deg C, 1 h, 2) 0 deg C, 1 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 9 steps<br /> </b>1: 73 percent / various solvent(s) / 0.08 h / Heating<br />2: 1) Li, liquid NH₃ / 1) THF, -78 deg C, 45 min, 2) -78 deg C, 30 min<br />3: 1) Hg(OCOCF₃)2, 2) aq. HCl / 1) CH₃NO₂, rt, 42 h, 2) rt, 1 h<br />4: 86 percent / aq. KOH / methanol / 1.5 h / Ambient temperature<br />5: 54 percent / D-camphor-10-sulfonic acid / benzene / 3 h / Heating<br />6: 80 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 &deg;C<br />7: 83 percent / DMSO, oxalyl chloride, NEt₃ / 1) CH₂Cl₂, -78 deg C, 1 h, 2) 0 deg C, 1 h<br />8: 1) n-butyllithium / 1) THF, hexane, -78 deg C, 4 min, 2) -78 deg C, 30 min<br />9: 72 percent / DMSO, oxalyl chloride, NEt₃ / 1) CH₂Cl₂, -78 deg C, 1 h, 2) 0 deg C, 1 h<br /> <br /> &nbsp;