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inquiry(R)-(+)-2-(4-methylphenylsulfonyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
With samarium diiodide; water; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; | 99% |
With ammonia; sodium In tetrahydrofuran at -78℃; for 0.75h; | 68% |
(R)-2-benzyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
With hydrogenchloride; 5%-palladium/activated carbon; hydrogen In ethanol; ethyl acetate at 20℃; under 760.051 Torr; for 24h; Schlenk technique; | 98% |
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
With water; sodium hydroxide In ethyl acetate at 20℃; | 97.9% |
1-phenylisoquinoline
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; trichloroisocyanuric acid; hydrogen; (R)-segphos In tetrahydrofuran at 80℃; under 62059.4 Torr; for 48h; Catalytic behavior; Reagent/catalyst; Solvent; Autoclave; enantioselective reaction; | 96% |
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; trichloroisocyanuric acid; hydrogen; (R)-segphos In tetrahydrofuran at 80℃; under 62059.4 Torr; for 48h; Catalytic behavior; Reagent/catalyst; Solvent; Glovebox; Autoclave; | 96% |
Multi-step reaction with 3 steps 1: acetone / 24 h / 90 °C 2: bis(1,5-cyclooctadiene)diiridium(I) dichloride; hydrogen; (Rax,S,S)-C3-TunePhos / dichloromethane; tetrahydrofuran / 20 h / 30 °C / 31029.7 Torr / Autoclave; Glovebox 3: hydrogen; hydrogenchloride; 5%-palladium/activated carbon / ethanol; ethyl acetate / 24 h / 20 °C / 760.05 Torr / Schlenk technique View Scheme | |
Multi-step reaction with 3 steps 1: acetone / 24 h / 90 °C 2: bis(1,5-cyclooctadiene)diiridium(I) dichloride; hydrogen; (+)-(R)-[2,3,2',3'-tetrahydro-5,5'-bi(1,4-benzodioxin)-6,6'-diyl]bis(diphenylphosphane) / dichloromethane; tetrahydrofuran / 20 h / 30 °C / 31029.7 Torr / Autoclave; Glovebox 3: hydrogen; hydrogenchloride; 5%-palladium/activated carbon / ethanol; ethyl acetate / 24 h / 20 °C / 760.05 Torr / Schlenk technique View Scheme |
1-phenyl-3,4-dihydroisoquinoline
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Stage #1: 1-phenyl-3,4-dihydroisoquinoline With N-Bromosuccinimide; bis(1,5-cyclooctadiene)diiridium(I) dichloride; sodium carbonate; (+)-(R)-[2,3,2',3'-tetrahydro-5,5'-bi(1,4-benzodioxin)-6,6'-diyl]bis(diphenylphosphane) In 1,2-dichloro-ethane at 20℃; for 0.166667h; Stage #2: With hydrogen In 1,2-dichloro-ethane at 30℃; under 25858.1 Torr; for 24h; enantioselective reaction; | 94% |
With N-Bromosuccinimide; bis(1,5-cyclooctadiene)diiridium(I) dichloride; hydrogen; sodium carbonate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl In 1,2-dichloro-ethane at 30℃; under 25858.1 Torr; for 24h; Glovebox; enantioselective reaction; | 94% |
With N-Bromosuccinimide; chloro(1,5-cyclooctadiene)rhodium(I) dimer; hydrogen; sodium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,2-dichloro-ethane at 30℃; under 25858.1 Torr; for 24h; Glovebox; enantioselective reaction; | 94% |
1-phenyl-1,2,3,4-tetrahydroisoquinoline
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Stage #1: 1-phenyl-1,2,3,4-tetrahydroisoquinoline With N-Bromosuccinimide; bis(1,5-cyclooctadiene)diiridium(I) dichloride; sodium carbonate; (+)-(R)-[2,3,2',3'-tetrahydro-5,5'-bi(1,4-benzodioxin)-6,6'-diyl]bis(diphenylphosphane) In 1,2-dichloro-ethane at 20℃; for 0.166667h; Stage #2: With hydrogen In 1,2-dichloro-ethane at 30℃; under 25858.1 Torr; for 24h; enantioselective reaction; | 93% |
With L-(-)-tartaric acid In methanol Resolution of racemate; | |
With potassium hydroxide In water; dimethyl sulfoxide for 11.8333h; Purification / work up; Heating / reflux; |
1-phenyl-1,2,3,4-tetrahydroisoquinoline
A
(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
B
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
With borane-ammonia complex; 6-hydroxy-D-nicotine oxidase E350L/E352D mutant for 120h; Kinetics; Enzymatic reaction; enantioselective reaction; | A n/a B 86% |
With D-tartaric acid Resolution of racemate; | A 79% B 2.78 g |
Stage #1: 1-phenyl-1,2,3,4-tetrahydroisoquinoline With D-tartaric acid In water Resolution of racemate; Stage #2: With sodium hydroxide In water at 20℃; Purification / work up; | A n/a B n/a |
(1R)-N-(8-menthyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Stage #1: (1R)-N-(8-menthyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline With 3 A molecular sieve; sodium acetate; pyridinium chlorochromate In dichloromethane at 20℃; for 48h; Stage #2: With potassium hydroxide In tetrahydrofuran Further stages.; | 82% |
(1E)-4-hydroxy-1-mesityl-4-methylpent-1-en-3-one
1-phenyl-1,2,3,4-tetrahydroisoquinoline
A
(1S)-2-(3-mesitylpropanoyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
B
(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
C
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
With 2-(2,4,6-trimethyl-phenyl)-2,5,6,7-tetrahydro-pyrrolo[2,1-c] [1,2,4]triazol-4-ylium perchlorate; (4aR,9aS)-4-hydroxy-4,4a,9,9a-tetrahydroindeno[2,1-b][1,4]oxazin-3(2H)-one; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 23℃; for 18h; Inert atmosphere; Resolution of racemate; optical yield given as %ee; enantioselective reaction; | A 49% B n/a C n/a |
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether at 0℃; for 48h; | 42% |
With lithium aluminium tetrahydride In diethyl ether at 0℃; for 48h; Yield given; |
(1S,5R)-5,8,8-trimethyl-1-[(1R)-1-phenyl-1,2,3,4-tetrahydroisoquinolin-2-ylcarbonyl]-3-oxabicyclo[3.2.1]octan-2-one
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
With Li[AlH2(OCH3)2] In tetrahydrofuran at -50℃; for 72h; | 35% |
1-phenyl-3,4-dihydroisoquinoline
A
(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
B
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
With sodium tetrahydroborate In ethanol at 20℃; for 60h; | |
With hydrogen; bis(1,5-cyclooctadiene)diiridium(I) dichloride; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine) In tetrahydrofuran; 1,1-dichloroethane at 20 - 50℃; under 22502.3 Torr; Product distribution / selectivity; Inert atmosphere; | A n/a B n/a |
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)diiridium(I) dichloride; hydrogen; iodine In dichloromethane at 20℃; under 38002.6 Torr; for 24h; Inert atmosphere; Autoclave; optical yield given as %ee; enantioselective reaction; |
N-phenethylbenzamide
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: P2O5; POCl3 / xylene / 2.5 h / Heating 2: NaBH4 / ethanol / 60 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: PPA / water / 4.25 h / 14.9 - 165 °C 1.2: 0.17 h / 28 - 42 °C / pH 2.1 - 7.12 2.1: methanol; sodium tetrahydroborate / water / 5.42 h / 20 - 34 °C 3.1: potassium hydroxide / water; dimethyl sulfoxide / 11.83 h / Heating / reflux View Scheme |
2-bromophenylacetaldehyde
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: 97 percent / CH2Cl2 / 20 °C 2.1: NaBH4; BF3*OEt2 / tetrahydrofuran / 2 h / 20 °C 2.2: 90 percent / NaOH / H2O / 1 h / Heating 3.1: 85 percent / 120 °C 4.1: t-BuLi / diethyl ether; pentane / 0.17 h / -90 °C 4.2: 78 percent / Et2AlCl / hexane / -90 - 20 °C 5.1: PCC; NaOAc; 3A molecular sieves / CH2Cl2 / 48 h / 20 °C 5.2: 82 percent / KOH / tetrahydrofuran View Scheme |
ortho-bromobenzaldehyde
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: potassium tert-butoxide / tetrahydrofuran / 0.5 h / 0 °C 1.2: tetrahydrofuran / 12 h / 20 °C 1.3: 95 percent / formic acid / CH2Cl2 / 72 h / 20 °C 2.1: 97 percent / CH2Cl2 / 20 °C 3.1: NaBH4; BF3*OEt2 / tetrahydrofuran / 2 h / 20 °C 3.2: 90 percent / NaOH / H2O / 1 h / Heating 4.1: 85 percent / 120 °C 5.1: t-BuLi / diethyl ether; pentane / 0.17 h / -90 °C 5.2: 78 percent / Et2AlCl / hexane / -90 - 20 °C 6.1: PCC; NaOAc; 3A molecular sieves / CH2Cl2 / 48 h / 20 °C 6.2: 82 percent / KOH / tetrahydrofuran View Scheme |
2α-(2'-bromophenylmethyl)-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: NaBH4; BF3*OEt2 / tetrahydrofuran / 2 h / 20 °C 1.2: 90 percent / NaOH / H2O / 1 h / Heating 2.1: 85 percent / 120 °C 3.1: t-BuLi / diethyl ether; pentane / 0.17 h / -90 °C 3.2: 78 percent / Et2AlCl / hexane / -90 - 20 °C 4.1: PCC; NaOAc; 3A molecular sieves / CH2Cl2 / 48 h / 20 °C 4.2: 82 percent / KOH / tetrahydrofuran View Scheme |
N-[(2'-bromophenyl)ethyl]-8-aminomenthol
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 85 percent / 120 °C 2.1: t-BuLi / diethyl ether; pentane / 0.17 h / -90 °C 2.2: 78 percent / Et2AlCl / hexane / -90 - 20 °C 3.1: PCC; NaOAc; 3A molecular sieves / CH2Cl2 / 48 h / 20 °C 3.2: 82 percent / KOH / tetrahydrofuran View Scheme |
3-[(2'-bromophenyl)ethyl]-2α-phenyl-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: t-BuLi / diethyl ether; pentane / 0.17 h / -90 °C 1.2: 78 percent / Et2AlCl / hexane / -90 - 20 °C 2.1: PCC; NaOAc; 3A molecular sieves / CH2Cl2 / 48 h / 20 °C 2.2: 82 percent / KOH / tetrahydrofuran View Scheme |
phenyl N-tosyl imine
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 1.) n-butyllithium / 1.) hexane, THF, -100 deg C, 15 min, 2.) THF, -85 to -100 deg C, 6 h 2: 48 percent / p-TsOH, conc. HCl / methanol; H2O / 96 h / Heating 3: 90 percent / LiAlH4 / tetrahydrofuran / 16 h / Heating 4: 68 percent / Na, liquid ammonia / tetrahydrofuran / 0.75 h / -78 °C View Scheme |
(4R,5R)-2-(2-Bromo-benzyl)-4,5-bis-(1-methoxy-1-methyl-ethyl)-[1,3]dioxolane
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 1.) n-butyllithium / 1.) hexane, THF, -100 deg C, 15 min, 2.) THF, -85 to -100 deg C, 6 h 2: 48 percent / p-TsOH, conc. HCl / methanol; H2O / 96 h / Heating 3: 90 percent / LiAlH4 / tetrahydrofuran / 16 h / Heating 4: 68 percent / Na, liquid ammonia / tetrahydrofuran / 0.75 h / -78 °C View Scheme | |
Multi-step reaction with 6 steps 1: 1.) n-butyllithium / 1.) hexane, THF, -100 deg, 2 h, 2.) THF, 0 deg C, 2 h 2: 53 percent / ammonium cerium(IV) nitrate / methanol; H2O / 3 h / Ambient temperature 3: 81 percent / Et3N / tetrahydrofuran / 8 h / Ambient temperature 4: 48 percent / p-TsOH, conc. HCl / methanol; H2O / 96 h / Heating 5: 90 percent / LiAlH4 / tetrahydrofuran / 16 h / Heating 6: 68 percent / Na, liquid ammonia / tetrahydrofuran / 0.75 h / -78 °C View Scheme |
4-methoxy-N-[(E)-phenylmethylidene]aniline
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 1.) n-butyllithium / 1.) hexane, THF, -100 deg, 2 h, 2.) THF, 0 deg C, 2 h 2: 53 percent / ammonium cerium(IV) nitrate / methanol; H2O / 3 h / Ambient temperature 3: 81 percent / Et3N / tetrahydrofuran / 8 h / Ambient temperature 4: 48 percent / p-TsOH, conc. HCl / methanol; H2O / 96 h / Heating 5: 90 percent / LiAlH4 / tetrahydrofuran / 16 h / Heating 6: 68 percent / Na, liquid ammonia / tetrahydrofuran / 0.75 h / -78 °C View Scheme |
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 53 percent / ammonium cerium(IV) nitrate / methanol; H2O / 3 h / Ambient temperature 2: 81 percent / Et3N / tetrahydrofuran / 8 h / Ambient temperature 3: 48 percent / p-TsOH, conc. HCl / methanol; H2O / 96 h / Heating 4: 90 percent / LiAlH4 / tetrahydrofuran / 16 h / Heating 5: 68 percent / Na, liquid ammonia / tetrahydrofuran / 0.75 h / -78 °C View Scheme |
(-)-N-<(αR)-2-<<(4R,5R)-4,5-bis(2-methoxypropan-2-yl)-1,3-dioxolan-2-yl>methyl>benzhydryl>-4-methylbenzenesulfonamide
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 48 percent / p-TsOH, conc. HCl / methanol; H2O / 96 h / Heating 2: 90 percent / LiAlH4 / tetrahydrofuran / 16 h / Heating 3: 68 percent / Na, liquid ammonia / tetrahydrofuran / 0.75 h / -78 °C View Scheme |
(R)-(+)-2-(4-methylphenylsulfonyl)-1-phenyl-1,2-dihydroisoquinoline
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 90 percent / LiAlH4 / tetrahydrofuran / 16 h / Heating 2: 68 percent / Na, liquid ammonia / tetrahydrofuran / 0.75 h / -78 °C View Scheme |
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 81 percent / Et3N / tetrahydrofuran / 8 h / Ambient temperature 2: 48 percent / p-TsOH, conc. HCl / methanol; H2O / 96 h / Heating 3: 90 percent / LiAlH4 / tetrahydrofuran / 16 h / Heating 4: 68 percent / Na, liquid ammonia / tetrahydrofuran / 0.75 h / -78 °C View Scheme |
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 13 percent / H2 / Pd/C / ethanol / 48 h 2: 42 percent / LiAlH4 / diethyl ether / 48 h / 0 °C View Scheme | |
Multi-step reaction with 2 steps 1: H2 / Pd/C / ethanol / 48 h / Ambient temperature 2: LiAlH4 / diethyl ether / 48 h / 0 °C View Scheme |
4-nitrophenyl-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate
A
(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
B
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Stage #1: 4-nitrophenyl-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate With sodium hydroxide In ethanol at 75 - 80℃; Stage #2: With water Cooling; |
N-chloroacetyl-(1R)-phenyl-1,2,3,4-tetrahydroisoquinoline
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: hydrogenchloride; water; phosphoric acid / 95 - 100 °C 1.2: 20 °C / pH 9 - 10 2.1: D-tartaric acid / water / Resolution of racemate 2.2: 20 °C View Scheme |
N-phenethylbenzamide
A
(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
B
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 2-chloropyridine; trifluoromethylsulfonic anhydride / dichloromethane / -78 - 20 °C / Inert atmosphere 2: 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)diiridium(I) dichloride; hydrogen; iodine / dichloromethane / 24 h / 20 °C / 38002.6 Torr / Inert atmosphere; Autoclave View Scheme | |
Multi-step reaction with 2 steps 1.1: phosphorus pentoxide; trichlorophosphate / 5,5-dimethyl-1,3-cyclohexadiene / 5 h / 140 °C 1.2: 1 h 2.1: bis(1,5-cyclooctadiene)diiridium(I) dichloride; phosphoric acid; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; potassium iodide / tetrahydrofuran / 16 h / 50 °C / 22502.3 Torr View Scheme | |
Multi-step reaction with 3 steps 1.1: phosphorus pentoxide; trichlorophosphate / 5,5-dimethyl-1,3-cyclohexadiene / 5 h / 140 °C 1.2: 1 h 2.1: palladium on activated charcoal; hydrogen / 30 °C / 3750.38 Torr 3.1: trifluoroacetic acid / methanol; ethanol; hexane / 25 °C / Resolution of racemate View Scheme |
benzoyl chloride
A
(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
B
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 0 - 20 °C 2: 2-chloropyridine; trifluoromethylsulfonic anhydride / dichloromethane / -78 - 20 °C / Inert atmosphere 3: 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)diiridium(I) dichloride; hydrogen; iodine / dichloromethane / 24 h / 20 °C / 38002.6 Torr / Inert atmosphere; Autoclave View Scheme | |
Multi-step reaction with 3 steps 1.1: dichloromethane / 2 h / 0 - 5 °C 1.2: 6 h / 0 °C / Reflux 2.1: phosphorus pentoxide; trichlorophosphate / 5,5-dimethyl-1,3-cyclohexadiene / 5 h / 140 °C 2.2: 1 h 3.1: bis(1,5-cyclooctadiene)diiridium(I) dichloride; phosphoric acid; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; potassium iodide / tetrahydrofuran / 16 h / 50 °C / 22502.3 Torr View Scheme | |
Multi-step reaction with 4 steps 1.1: dichloromethane / 2 h / 0 - 5 °C 1.2: 6 h / 0 °C / Reflux 2.1: phosphorus pentoxide; trichlorophosphate / 5,5-dimethyl-1,3-cyclohexadiene / 5 h / 140 °C 2.2: 1 h 3.1: palladium on activated charcoal; hydrogen / 30 °C / 3750.38 Torr 4.1: trifluoroacetic acid / methanol; ethanol; hexane / 25 °C / Resolution of racemate View Scheme |
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
1-phenyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
With water; potassium hydroxide In dimethyl sulfoxide at 120℃; for 10h; | 92.1% |
With potassium hydroxide; water In dimethyl sulfoxide at 160℃; for 15h; | |
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / -10 - 20 °C 2.1: hydrogenchloride; water; phosphoric acid / 95 - 100 °C 2.2: 20 °C / pH 9 - 10 View Scheme |
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
1-phenyl-3,4-dihydroisoquinoline
Conditions | Yield |
---|---|
With dimethyl sulfoxide at 100℃; for 24h; Solvent; Temperature; Schlenk technique; Green chemistry; chemoselective reaction; | 87% |
Multi-step reaction with 2 steps 1: trichloroisocyanuric acid / dichloromethane / 1.5 h / 3 - 5 °C 2: potassium hydroxide / methanol / 1 h / 20 °C View Scheme | |
With hydrogenchloride; oxygen In aq. phosphate buffer at 37℃; pH=7.8; | |
With air In N,N-dimethyl-formamide at 100℃; for 24h; Schlenk technique; Green chemistry; |
chloroformic acid ethyl ester
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
ethyl (R)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate
Conditions | Yield |
---|---|
With potassium carbonate In dichloromethane at 20℃; |
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
(3S)-1-azabicyclo[2.2.2]oct-3-yl (1R)-3,4-dihydro-1-phenyl-2(1H)-isoquinolinecarboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: K2CO3 / CH2Cl2 / 20 °C 2: NaH / toluene / Heating View Scheme |
(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
(3R)-1-azabicyclo[2.2.2]oct-3-yl (1R)-3,4-dihydro-1-phenyl-2(1H)-isoquinolinecarboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: K2CO3 / CH2Cl2 / 20 °C 2: NaH / toluene / Heating View Scheme |
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