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[ CAS No. 55469-90-4 ] {[proInfo.proName]}

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Chemical Structure| 55469-90-4
Chemical Structure| 55469-90-4
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Product Details of [ 55469-90-4 ]

CAS No. :55469-90-4 MDL No. :MFCD09834139
Formula : C9H10N2O Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 162.19 Pubchem ID :-
Synonyms :

Safety of [ 55469-90-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 55469-90-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 55469-90-4 ]

[ 55469-90-4 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 7521-41-7 ]
  • [ 55469-90-4 ]
  • [ 80364-37-0 ]
YieldReaction ConditionsOperation in experiment
71.9% With hydrogenchloride In ethanol for 24h; Ambient temperature;
  • 2
  • [ 551-93-9 ]
  • [ 55469-90-4 ]
  • [ 76628-97-2 ]
YieldReaction ConditionsOperation in experiment
60.5% With hydrogenchloride In ethanol for 24h; Ambient temperature;
  • 3
  • [ 79-19-6 ]
  • [ 55469-90-4 ]
  • [ 82070-64-2 ]
YieldReaction ConditionsOperation in experiment
89% With hydrogenchloride In ethanol for 3h; Heating;
  • 4
  • [ 2835-77-0 ]
  • [ 55469-90-4 ]
  • [ 76629-00-0 ]
YieldReaction ConditionsOperation in experiment
88% With hydrogenchloride In ethanol for 24h; Ambient temperature;
  • 5
  • [ 140-87-4 ]
  • [ 55469-90-4 ]
  • [ 82070-70-0 ]
YieldReaction ConditionsOperation in experiment
75% With hydrogenchloride In ethanol for 3h; Heating;
  • 6
  • [ 563-41-7 ]
  • [ 55469-90-4 ]
  • [ 82070-56-2 ]
YieldReaction ConditionsOperation in experiment
74% In ethanol for 3h; Heating;
  • 7
  • [ 55469-90-4 ]
  • [ 130687-75-1 ]
YieldReaction ConditionsOperation in experiment
With hydroxylamine hydrochloride In pyridine; ethanol for 1.5h; Heating;
  • 8
  • [ 55469-90-4 ]
  • [ 82070-53-9 ]
YieldReaction ConditionsOperation in experiment
92% With hydrazine hydrate for 2h; Heating;
  • 9
  • [ 298-12-4 ]
  • [ 55469-90-4 ]
  • [ 700364-86-9 ]
YieldReaction ConditionsOperation in experiment
46% With potassium hydroxide In ethanol for 1h; Heating;
  • 10
  • [ 24424-99-5 ]
  • [ 55469-90-4 ]
  • [ 959992-91-7 ]
YieldReaction ConditionsOperation in experiment
77% In tetrahydrofuran at 50℃; 44 The starting material, /er/-butyl 7-(2 -hydroxy ethyl)-4-methyl-3,4-dihydro- 1,8- naphthyridine-l(2H)-carboxylate was prepared according to the following scheme:To a solution of 7-methyl-2,3-dihydro-lH-l,8-naphthyridin-4-one (590 mg, 3.64 mmol) (Journal of Heterocyclic Chemistry 1996, 33(4), 1185-1189) in THF (8 ml) were added catalytic DMAP (44 mg, 0.36 mmol) and BOC2O (1.03 g, 4.73 mmol). The reaction mixture was stirred overnight at 5O0C. After removal of solvent, the residue was purified by silica gel flash chromatography (20 to 35% ethyl acetate in petroleum ether) to give tert-butyl 7-methyl-4-oxo-3,4-dihydro-l,8-naphthyridine-l(2H)-carboxylate as a solid (736 mg, 77%); 1H NMR Spectrum (CDC13) 1.56 (s, 9H), 2.56 (s, 3H), 2.76 (t, 2H), 4.14 (t, 2H), 6.99 (d, IH), 8.13 (d, IH).
  • 11
  • [ 55469-90-4 ]
  • [ 82070-72-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 92 percent / 85 percent aq. hydrazine / 2 h / Heating 2: 77 percent / conc. ammonia / H2O / 24 h / Ambient temperature
  • 12
  • [ 55469-90-4 ]
  • [ 82070-86-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 92 percent / 85 percent aq. hydrazine / 2 h / Heating 2: 84 percent / conc. ammonia / H2O; ethanol / 24 h / Ambient temperature
  • 13
  • [ 55469-90-4 ]
  • [ 82070-89-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 92 percent / 85 percent aq. hydrazine / 2 h / Heating 2: 95 percent / conc. ammonia / H2O / 24 h / Ambient temperature
  • 14
  • [ 55469-90-4 ]
  • [ 82070-78-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 92 percent / 85 percent aq. hydrazine / 2 h / Heating 2: 89 percent / conc. ammonia / H2O; ethanol / 24 h / Ambient temperature
  • 15
  • [ 55469-90-4 ]
  • [ 82070-74-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 92 percent / 85 percent aq. hydrazine / 2 h / Heating 2: 83 percent / conc. ammonia / H2O / 24 h / Ambient temperature
  • 16
  • [ 55469-90-4 ]
  • [ 82070-76-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 92 percent / 85 percent aq. hydrazine / 2 h / Heating 2: 86 percent / conc. ammonia / H2O; ethanol / 1.) 50 deg C, 8 h; 2.) room temp., overnight
  • 17
  • [ 55469-90-4 ]
  • [ 82070-80-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 92 percent / 85 percent aq. hydrazine / 2 h / Heating 2: 65 percent / conc. ammonia / H2O; ethanol / 24 h / Ambient temperature
  • 18
  • [ 55469-90-4 ]
  • [ 82070-82-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 92 percent / 85 percent aq. hydrazine / 2 h / Heating 2: 91 percent / conc. ammonia / H2O; ethanol / 24 h / Ambient temperature
  • 19
  • [ 55469-90-4 ]
  • [ 82070-88-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 92 percent / 85 percent aq. hydrazine / 2 h / Heating 2: 87 percent / conc. ammonia / H2O; ethanol / 24 h / Ambient temperature
  • 20
  • [ 55469-90-4 ]
  • [ 82070-84-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 92 percent / 85 percent aq. hydrazine / 2 h / Heating 2: 88 percent / conc. ammonia / H2O; ethanol / 24 h / Ambient temperature
  • 21
  • [ 55469-90-4 ]
  • [ 130687-78-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride / ethanol; pyridine / 1.5 h / Heating 2: 85 percent / hydrogen chloride / CHCl3 / 5 h / 0 °C 3: 69 percent / N-bromosuccinimide (NBS) / CHCl3 / 1.5 h / Heating
  • 22
  • [ 55469-90-4 ]
  • [ 130687-80-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride / ethanol; pyridine / 1.5 h / Heating 2: 85 percent / hydrogen chloride / CHCl3 / 5 h / 0 °C
  • 23
  • [ 55469-90-4 ]
  • [ 130875-74-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydroxylamine hydrochloride / ethanol; pyridine / 1.5 h / Heating 2: 85 percent / hydrogen chloride / CHCl3 / 5 h / 0 °C 3: 69 percent / N-bromosuccinimide (NBS) / CHCl3 / 1.5 h / Heating 4: 1.) sodium methoxide / 1.) methanol, reflux, 1 h, 2.) toluene, 100 deg C, 24 h
  • 24
  • [ 55469-90-4 ]
  • [ 130875-91-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydroxylamine hydrochloride / ethanol; pyridine / 1.5 h / Heating 2: 85 percent / hydrogen chloride / CHCl3 / 5 h / 0 °C 3: 69 percent / N-bromosuccinimide (NBS) / CHCl3 / 1.5 h / Heating 4: 1.) sodium methoxide / 1.) methanol, reflux, 1 h, 2.) toluene, 100 deg C, 24 h 5: 69 percent / toluene / 24 h / 80 °C
  • 25
  • [ 55469-90-4 ]
  • [ 130875-92-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydroxylamine hydrochloride / ethanol; pyridine / 1.5 h / Heating 2: 85 percent / hydrogen chloride / CHCl3 / 5 h / 0 °C 3: 69 percent / N-bromosuccinimide (NBS) / CHCl3 / 1.5 h / Heating 4: 1.) sodium methoxide / 1.) methanol, reflux, 1 h, 2.) toluene, 100 deg C, 24 h 5: 65 percent / toluene / 24 h / 80 °C
  • 26
  • [ 55469-90-4 ]
  • [ 130875-76-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride / ethanol; pyridine / 1.5 h / Heating 2: 85 percent / hydrogen chloride / CHCl3 / 5 h / 0 °C 3: 1.) sodium methoxide / 1.) methanol, reflux, 1 h, 2.) toluene, 100 deg C, 24 h
  • 27
  • [ 55469-90-4 ]
  • [ 130875-69-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride / ethanol; pyridine / 1.5 h / Heating 2: 85 percent / hydrogen chloride / CHCl3 / 5 h / 0 °C 3: 1.) sodium methoxide / 1.) methanol, reflux, 1 h, 2.) toluene, 100 deg C, 24 h
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride / ethanol; pyridine / 1.5 h / Heating 2: 1.) sodium methoxide / 1.) methanol, reflux, 1 h, 2.) toluene, 100 deg C, 24 h
  • 28
  • [ 55469-90-4 ]
  • [ 130875-95-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydroxylamine hydrochloride / ethanol; pyridine / 1.5 h / Heating 2: 85 percent / hydrogen chloride / CHCl3 / 5 h / 0 °C 3: 1.) sodium methoxide / 1.) methanol, reflux, 1 h, 2.) toluene, 100 deg C, 24 h 4: 73 percent / toluene / 24 h / 80 °C
  • 29
  • [ 55469-90-4 ]
  • [ 130875-81-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydroxylamine hydrochloride / ethanol; pyridine / 1.5 h / Heating 2: 85 percent / hydrogen chloride / CHCl3 / 5 h / 0 °C 3: 1.) sodium methoxide / 1.) methanol, reflux, 1 h, 2.) toluene, 100 deg C, 24 h 4: 81 percent / toluene / 24 h / 80 °C
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride / ethanol; pyridine / 1.5 h / Heating 2: 1.) sodium methoxide / 1.) methanol, reflux, 1 h, 2.) toluene, 100 deg C, 24 h 3: 81 percent / toluene / 24 h / 80 °C
  • 30
  • [ 55469-90-4 ]
  • [ 130875-82-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydroxylamine hydrochloride / ethanol; pyridine / 1.5 h / Heating 2: 85 percent / hydrogen chloride / CHCl3 / 5 h / 0 °C 3: 1.) sodium methoxide / 1.) methanol, reflux, 1 h, 2.) toluene, 100 deg C, 24 h 4: 85 percent / toluene / 24 h / 80 °C
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride / ethanol; pyridine / 1.5 h / Heating 2: 1.) sodium methoxide / 1.) methanol, reflux, 1 h, 2.) toluene, 100 deg C, 24 h 3: 85 percent / toluene / 24 h / 80 °C
  • 31
  • [ 55469-90-4 ]
  • [ 243641-37-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium tetrahydroborate; methanol / 1 h / 20 °C 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / methanol / 72 h 2.2: pH ~ 10 3.1: 18 h / 75 °C / Neat (no solvent)
Multi-step reaction with 3 steps 1: sodium tetrahydroborate; methanol / 1 h / 20 °C 2: hydrogen; acetic acid / palladium 10% on activated carbon / methanol / 72 h 3: dichloromethane / 18 h / 75 °C
Multi-step reaction with 3 steps 1.1: sodium tetrahydroborate; methanol / 1 h / 20 °C 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / methanol / 72 h 2.2: pH ~ 10 3.1: 18 h / 75 °C / Neat (no solvent)
  • 32
  • [ 55469-90-4 ]
  • [ 274676-47-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium tetrahydroborate; methanol / 1 h / 20 °C 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / methanol / 72 h 2.2: pH ~ 10
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; methanol / 1 h / 20 °C 2: hydrogen; acetic acid / palladium 10% on activated carbon / methanol / 72 h
Multi-step reaction with 2 steps 1.1: sodium tetrahydroborate; methanol / 1 h / 20 °C 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / methanol / 72 h 2.2: pH ~ 10
  • 33
  • [ 55469-90-4 ]
  • [ 243641-38-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium tetrahydroborate; methanol / 1 h / 20 °C 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / methanol / 72 h 2.2: pH ~ 10 3.1: 18 h / 75 °C / Neat (no solvent) 4.1: lithium diisopropyl amide / tetrahydrofuran / 0.67 h / -78 °C
Multi-step reaction with 4 steps 1.1: sodium tetrahydroborate; methanol / 1 h / 20 °C 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / methanol / 72 h 3.1: dichloromethane / 18 h / 75 °C 4.1: diisopropylamine; n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C 4.2: -8 °C
Multi-step reaction with 4 steps 1.1: sodium tetrahydroborate; methanol / 1 h / 20 °C 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / methanol / 72 h 2.2: pH ~ 10 3.1: 18 h / 75 °C / Neat (no solvent) 4.1: diisopropylamine; n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C
  • 34
  • [ 55469-90-4 ]
  • [ 1292955-81-7 ]
YieldReaction ConditionsOperation in experiment
90% With methanol; sodium tetrahydroborate at 20℃; for 1h; 9.B Step BThe title compound from Step A above (7 g, 43.2 mmol) was suspended in methanol (170 mL) and sodium borohydride (2.94 g, 77.7 mmol) was added in portions. After the addition was completed, the mixture was stirred at room temperature for 1 h to become a clear solution. Then acetic acid (21 mL) was added and the solvents were removed. The residue was dissolved in water (250 mL) and the aqueous phase was washed with dichloromethane (2×100 mL). The aqueous phase was made alkaline (pH 10) by adding sodium carbonate and extracted with ethyl acetate (6×150 mL). The combined organic phase was dried over Na2SO4, filtered and the solvents were removed to afford the title compound as an off-white solid (6.39 g, 90%).1H-NMR (400 MHz, CDCl3): δ=1.82-1.90 (m, 1H), 1.95-2.01 (m, 1H), 2.30 (s, 3H), 3.10 (br-s, 1H), 3.31-3.36 (m, 1H), 3.48 (dt, 1H), 4.72 (t, 1H), 5.32 (br-s, 1H), 6.38 (d, 1H), 7.32 (d, 1H)
90% With methanol; sodium tetrahydroborate at 20℃; for 1h; 9.B Step B The title compound from Step A above (7 g, 43.2 mmol) was suspended in methanol (170 mL) and sodium borohydride (2.94 g, 77.7 mmol) was added in portions. After the addition was completed, the mixture was stirred at room temperature for 1 h to become a clear solution. Then acetic acid (21 mL) was added and the solvents were removed. The residue was dissolved in water (250 mL) and the aqueous phase was washed with dichloromethane (2 x 100 mL). The aqueous phase was made alkaline (pH ∼10) by adding sodium carbonate and extracted with ethyl acetate (6 x 150 mL). The combined organic phase was dried over Na2SO4, filtered and the solvents were removed to afford the title compound as an off-white solid (6.39 g, 90 %). 1H-NMR (400 MHz, CDCl3): d = 1.82-1.90 (m, 1H), 1.95-2.01 (m, 1H), 2.30 (s, 3H), 3.10 (br-s, 1H), 3.31-3.36 (m, 1H). 3.48 (dt, 1H), 4.72 (t, 1H), 5.32 (br-s, 1H), 6.38 (d, 1H), 7.32 (d, 1H)
90% With methanol; sodium tetrahydroborate at 20℃; for 1h; 9.B The title compound from Step A above (7 g, 43.2 mmol) was suspended in methanol ( 170 mL) and sodium borohydride (2.94 g, 77.7 mmol) was added in portions. After the addition was completed, the mixture was stirred at room temperature for 1 h to become a clear solution. Then acetic acid (21 mL) was added and the solvents were removed. The residue was dissolved in water (250 mL) and the aqueous phase was washed with dichloromethane (2 x 100 mL). The aqueous phase was made alkaline (pH -10) by adding sodium carbonate and extracted with ethyl acetate (6 x 150 mL). The combined organic phase was dried over 'd;SO :. filtered and the solvents were removed to afford the title compound as an off-white solid (6.39 g, 90 %).-NMR (400 MHz, CDC13): d = 1.82-1 .90 (m, IH), 1.95-2.01 (m. 1H), 2.30 (s, 3H), 3.10 (br- s, 1 H), 3.31 -3.36 (m, I H), 3.48 (dt, I H), 4.72 (t, 1 H), 5.32 (br-s, 1 H), 6.38 (d, I H), 7.32 (d, 1H)
  • 35
  • [ 55469-90-4 ]
  • [ 855313-32-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium tetrahydroborate; methanol / 1 h / 20 °C 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / methanol / 72 h 2.2: pH ~ 10 3.1: 18 h / 75 °C / Neat (no solvent) 4.1: lithium diisopropyl amide / tetrahydrofuran / 0.67 h / -78 °C 5.1: potassium hexamethylsilazane / tetrahydrofuran / 0.75 h / -78 °C 5.2: 0.5 h / -78 °C 5.3: -78 - 20 °C
Multi-step reaction with 5 steps 1.1: sodium tetrahydroborate; methanol / 1 h / 20 °C 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / methanol / 72 h 3.1: dichloromethane / 18 h / 75 °C 4.1: diisopropylamine; n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C 4.2: -8 °C 5.1: potassium hexamethylsilazane / tetrahydrofuran / 0.75 h / -78 °C 5.2: 0.5 h / -78 °C 5.3: -78 - 20 °C
Multi-step reaction with 5 steps 1.1: sodium tetrahydroborate; methanol / 1 h / 20 °C 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / methanol / 72 h 2.2: pH ~ 10 3.1: 18 h / 75 °C / Neat (no solvent) 4.1: diisopropylamine; n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C 5.1: potassium hexamethylsilazane / tetrahydrofuran / 0.75 h / -78 °C 5.2: 0.5 h / -78 °C 5.3: -78 - 20 °C
  • 36
  • [ 55469-90-4 ]
  • [ 855313-33-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium tetrahydroborate; methanol / 1 h / 20 °C 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / methanol / 72 h 2.2: pH ~ 10 3.1: 18 h / 75 °C / Neat (no solvent) 4.1: lithium diisopropyl amide / tetrahydrofuran / 0.67 h / -78 °C 5.1: potassium hexamethylsilazane / tetrahydrofuran / 0.75 h / -78 °C 5.2: 0.5 h / -78 °C 5.3: -78 - 20 °C 6.1: ethanol; sodium tetrahydroborate / 0 °C
Multi-step reaction with 6 steps 1.1: sodium tetrahydroborate; methanol / 1 h / 20 °C 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / methanol / 72 h 3.1: dichloromethane / 18 h / 75 °C 4.1: diisopropylamine; n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C 4.2: -8 °C 5.1: potassium hexamethylsilazane / tetrahydrofuran / 0.75 h / -78 °C 5.2: 0.5 h / -78 °C 5.3: -78 - 20 °C 6.1: ethanol; sodium tetrahydroborate / 0 - 20 °C
Multi-step reaction with 6 steps 1.1: sodium tetrahydroborate; methanol / 1 h / 20 °C 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / methanol / 72 h 2.2: pH ~ 10 3.1: 18 h / 75 °C / Neat (no solvent) 4.1: diisopropylamine; n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C 5.1: potassium hexamethylsilazane / tetrahydrofuran / 0.75 h / -78 °C 5.2: 0.5 h / -78 °C 5.3: -78 - 20 °C 6.1: ethanol; sodium tetrahydroborate / 0 - 20 °C
  • 37
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  • [ 1292955-97-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: sodium tetrahydroborate; methanol / 1 h / 20 °C 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / methanol / 72 h 2.2: pH ~ 10 3.1: 18 h / 75 °C / Neat (no solvent) 4.1: lithium diisopropyl amide / tetrahydrofuran / 0.67 h / -78 °C 5.1: potassium hexamethylsilazane / tetrahydrofuran / 0.75 h / -78 °C 5.2: 0.5 h / -78 °C 5.3: -78 - 20 °C 6.1: ethanol; sodium tetrahydroborate / 0 °C 7.1: pyridine / acetonitrile / 0.5 h / 0 °C
Multi-step reaction with 7 steps 1.1: sodium tetrahydroborate; methanol / 1 h / 20 °C 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / methanol / 72 h 3.1: dichloromethane / 18 h / 75 °C 4.1: diisopropylamine; n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C 4.2: -8 °C 5.1: potassium hexamethylsilazane / tetrahydrofuran / 0.75 h / -78 °C 5.2: 0.5 h / -78 °C 5.3: -78 - 20 °C 6.1: ethanol; sodium tetrahydroborate / 0 - 20 °C 7.1: pyridine / acetonitrile / 0.5 h / 0 °C
Multi-step reaction with 7 steps 1.1: sodium tetrahydroborate; methanol / 1 h / 20 °C 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / methanol / 72 h 2.2: pH ~ 10 3.1: 18 h / 75 °C / Neat (no solvent) 4.1: diisopropylamine; n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C 5.1: potassium hexamethylsilazane / tetrahydrofuran / 0.75 h / -78 °C 5.2: 0.5 h / -78 °C 5.3: -78 - 20 °C 6.1: ethanol; sodium tetrahydroborate / 0 - 20 °C 7.1: pyridine / acetonitrile / 0.5 h / 0 °C
  • 38
  • [ 55469-90-4 ]
  • [ 1292955-99-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: sodium tetrahydroborate; methanol / 1 h / 20 °C 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / methanol / 72 h 2.2: pH ~ 10 3.1: 18 h / 75 °C / Neat (no solvent) 4.1: lithium diisopropyl amide / tetrahydrofuran / 0.67 h / -78 °C 5.1: potassium hexamethylsilazane / tetrahydrofuran / 0.75 h / -78 °C 5.2: 0.5 h / -78 °C 5.3: -78 - 20 °C 6.1: ethanol; sodium tetrahydroborate / 0 °C 7.1: pyridine / acetonitrile / 0.5 h / 0 °C 8.1: sodium azide / N,N-dimethyl acetamide / 3 h / 75 °C
Multi-step reaction with 8 steps 1.1: sodium tetrahydroborate; methanol / 1 h / 20 °C 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / methanol / 72 h 3.1: dichloromethane / 18 h / 75 °C 4.1: diisopropylamine; n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C 4.2: -8 °C 5.1: potassium hexamethylsilazane / tetrahydrofuran / 0.75 h / -78 °C 5.2: 0.5 h / -78 °C 5.3: -78 - 20 °C 6.1: ethanol; sodium tetrahydroborate / 0 - 20 °C 7.1: pyridine / acetonitrile / 0.5 h / 0 °C 8.1: sodium azide / ISOPROPYLAMIDE / 3 h / 75 °C
Multi-step reaction with 8 steps 1.1: sodium tetrahydroborate; methanol / 1 h / 20 °C 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / methanol / 72 h 2.2: pH ~ 10 3.1: 18 h / 75 °C / Neat (no solvent) 4.1: diisopropylamine; n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C 5.1: potassium hexamethylsilazane / tetrahydrofuran / 0.75 h / -78 °C 5.2: 0.5 h / -78 °C 5.3: -78 - 20 °C 6.1: ethanol; sodium tetrahydroborate / 0 - 20 °C 7.1: pyridine / acetonitrile / 0.5 h / 0 °C 8.1: sodium azide / ISOPROPYLAMIDE / 3 h / 75 °C
  • 39
  • [ 55469-90-4 ]
  • [ 1292956-00-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: sodium tetrahydroborate; methanol / 1 h / 20 °C 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / methanol / 72 h 2.2: pH ~ 10 3.1: 18 h / 75 °C / Neat (no solvent) 4.1: lithium diisopropyl amide / tetrahydrofuran / 0.67 h / -78 °C 5.1: potassium hexamethylsilazane / tetrahydrofuran / 0.75 h / -78 °C 5.2: 0.5 h / -78 °C 5.3: -78 - 20 °C 6.1: ethanol; sodium tetrahydroborate / 0 °C 7.1: pyridine / acetonitrile / 0.5 h / 0 °C 8.1: sodium azide / N,N-dimethyl acetamide / 3 h / 75 °C 9.1: triphenylphosphine / tetrahydrofuran / 20 h / 20 °C
Multi-step reaction with 9 steps 1.1: sodium tetrahydroborate; methanol / 1 h / 20 °C 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / methanol / 72 h 3.1: dichloromethane / 18 h / 75 °C 4.1: diisopropylamine; n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C 4.2: -8 °C 5.1: potassium hexamethylsilazane / tetrahydrofuran / 0.75 h / -78 °C 5.2: 0.5 h / -78 °C 5.3: -78 - 20 °C 6.1: ethanol; sodium tetrahydroborate / 0 - 20 °C 7.1: pyridine / acetonitrile / 0.5 h / 0 °C 8.1: sodium azide / ISOPROPYLAMIDE / 3 h / 75 °C 9.1: triphenylphosphine / tetrahydrofuran / 20 h / 20 °C
Multi-step reaction with 9 steps 1.1: sodium tetrahydroborate; methanol / 1 h / 20 °C 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / methanol / 72 h 2.2: pH ~ 10 3.1: 18 h / 75 °C / Neat (no solvent) 4.1: diisopropylamine; n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C 5.1: potassium hexamethylsilazane / tetrahydrofuran / 0.75 h / -78 °C 5.2: 0.5 h / -78 °C 5.3: -78 - 20 °C 6.1: ethanol; sodium tetrahydroborate / 0 - 20 °C 7.1: pyridine / acetonitrile / 0.5 h / 0 °C 8.1: sodium azide / ISOPROPYLAMIDE / 3 h / 75 °C 9.1: triphenylphosphine / tetrahydrofuran / 20 h / 20 °C
  • 40
  • [ 55469-90-4 ]
  • [ 1292956-02-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: sodium tetrahydroborate; methanol / 1 h / 20 °C 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / methanol / 72 h 2.2: pH ~ 10 3.1: 18 h / 75 °C / Neat (no solvent) 4.1: lithium diisopropyl amide / tetrahydrofuran / 0.67 h / -78 °C 5.1: potassium hexamethylsilazane / tetrahydrofuran / 0.75 h / -78 °C 5.2: 0.5 h / -78 °C 5.3: -78 - 20 °C 6.1: ethanol; sodium tetrahydroborate / 0 °C 7.1: pyridine / acetonitrile / 0.5 h / 0 °C 8.1: sodium azide / N,N-dimethyl acetamide / 3 h / 75 °C 9.1: triphenylphosphine / tetrahydrofuran / 20 h / 20 °C 10.1: sodium t-butanolate / 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0) chloroform complex / toluene / 0.75 h / 115 °C / Inert atmosphere; Sealed vial
Multi-step reaction with 10 steps 1.1: sodium tetrahydroborate; methanol / 1 h / 20 °C 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / methanol / 72 h 3.1: dichloromethane / 18 h / 75 °C 4.1: diisopropylamine; n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C 4.2: -8 °C 5.1: potassium hexamethylsilazane / tetrahydrofuran / 0.75 h / -78 °C 5.2: 0.5 h / -78 °C 5.3: -78 - 20 °C 6.1: ethanol; sodium tetrahydroborate / 0 - 20 °C 7.1: pyridine / acetonitrile / 0.5 h / 0 °C 8.1: sodium azide / ISOPROPYLAMIDE / 3 h / 75 °C 9.1: triphenylphosphine / tetrahydrofuran / 20 h / 20 °C 10.1: sodium t-butanolate / 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0) chloroform complex / toluene / 0.75 h / 115 °C / Inert atmosphere; Sealed tube
Multi-step reaction with 10 steps 1.1: sodium tetrahydroborate; methanol / 1 h / 20 °C 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / methanol / 72 h 2.2: pH ~ 10 3.1: 18 h / 75 °C / Neat (no solvent) 4.1: diisopropylamine; n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C 5.1: potassium hexamethylsilazane / tetrahydrofuran / 0.75 h / -78 °C 5.2: 0.5 h / -78 °C 5.3: -78 - 20 °C 6.1: ethanol; sodium tetrahydroborate / 0 - 20 °C 7.1: pyridine / acetonitrile / 0.5 h / 0 °C 8.1: sodium azide / ISOPROPYLAMIDE / 3 h / 75 °C 9.1: triphenylphosphine / tetrahydrofuran / 20 h / 20 °C 10.1: sodium t-butanolate / 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0) chloroform complex / toluene / 0.75 h / 115 °C / Inert atmosphere; Sealed vessel
  • 41
  • [ 55469-90-4 ]
  • [ 1292956-08-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: sodium tetrahydroborate; methanol / 1 h / 20 °C 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / methanol / 72 h 2.2: pH ~ 10 3.1: 18 h / 75 °C / Neat (no solvent) 4.1: lithium diisopropyl amide / tetrahydrofuran / 0.67 h / -78 °C 5.1: potassium hexamethylsilazane / tetrahydrofuran / 0.75 h / -78 °C 5.2: 0.5 h / -78 °C 5.3: -78 - 20 °C 6.1: ethanol; sodium tetrahydroborate / 0 °C 7.1: pyridine / acetonitrile / 0.5 h / 0 °C 8.1: sodium azide / N,N-dimethyl acetamide / 3 h / 75 °C 9.1: triphenylphosphine / tetrahydrofuran / 20 h / 20 °C 10.1: sodium t-butanolate / 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0) chloroform complex / toluene / 0.75 h / 115 °C / Inert atmosphere; Sealed vial
Multi-step reaction with 10 steps 1.1: sodium tetrahydroborate; methanol / 1 h / 20 °C 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / methanol / 72 h 3.1: dichloromethane / 18 h / 75 °C 4.1: diisopropylamine; n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C 4.2: -8 °C 5.1: potassium hexamethylsilazane / tetrahydrofuran / 0.75 h / -78 °C 5.2: 0.5 h / -78 °C 5.3: -78 - 20 °C 6.1: ethanol; sodium tetrahydroborate / 0 - 20 °C 7.1: pyridine / acetonitrile / 0.5 h / 0 °C 8.1: sodium azide / ISOPROPYLAMIDE / 3 h / 75 °C 9.1: triphenylphosphine / tetrahydrofuran / 20 h / 20 °C 10.1: sodium t-butanolate / 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0) chloroform complex / toluene / 0.75 h / 115 °C / Inert atmosphere; Sealed tube
Multi-step reaction with 10 steps 1.1: sodium tetrahydroborate; methanol / 1 h / 20 °C 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / methanol / 72 h 2.2: pH ~ 10 3.1: 18 h / 75 °C / Neat (no solvent) 4.1: diisopropylamine; n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C 5.1: potassium hexamethylsilazane / tetrahydrofuran / 0.75 h / -78 °C 5.2: 0.5 h / -78 °C 5.3: -78 - 20 °C 6.1: ethanol; sodium tetrahydroborate / 0 - 20 °C 7.1: pyridine / acetonitrile / 0.5 h / 0 °C 8.1: sodium azide / ISOPROPYLAMIDE / 3 h / 75 °C 9.1: triphenylphosphine / tetrahydrofuran / 20 h / 20 °C 10.1: sodium t-butanolate / 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0) chloroform complex / toluene / 0.75 h / 115 °C / Inert atmosphere; Sealed vessel
  • 42
  • [ 55469-89-1 ]
  • [ 55469-90-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: <i>N</i>-(6-methyl-[2]pyridyl)-β-alanine With chlorosulfonic acid In dichloromethane at 20℃; for 2h; Cooling with ice; Stage #2: With sodium carbonate; sodium hydroxide In dichloromethane; water 9.A Step ATo commercially available 2-amino-6-methylpyridine (25.46 g, 235 mmol) was added ethyl acrylate (26 mL, 239 mmol) and acetic acid (6 mL, 105 mmol). This mixture was heated at 150° C. in a sand bath for 50 h. The mixture was cooled to room temperature and 6 N sodium hydroxide (120 mL, 720 mmol) was added. The mixture was then heated at 120° C. in a sand bath for 1 h. The mixture was cooled to room temperature and concentrated hydrochloric acid was added until the pH reached approx. 4-5 with ice-cooling. A polymeric precipitate was formed and the mixture was filtered. The filtrate was evaporated and the residue was treated with methanol (100 mL). The resulting slurry was stirred at room temperature for 30 minutes and filtered. The precipitate was washed with methanol (30 mL) and the combined filtrates were evaporated to leave a brownish, sticky mass. This crude material was dissolved in dichloromethane (400 mL) and the solution was placed in an ice-bath. Then chlorosulfonic acid (162 mL, 2430 mmol) was added dropwise. After the addition was completed, the mixture was stirred at room temperature for 2 h. Then the mixture was placed back into the ice-bath and water (800 mL) was carefully added. After the addition was completed, the acidic solution was made alkaline to pH 6 by adding sodium hydroxide. Then sodium carbonate was added to adjust the pH to 10 to 11. A precipitate was formed and the mixture was extracted with ethyl acetate (3×400 mL). The organic phase was separated, dried over Na2SO4, filtered and the solvents were removed. The residue was purified by chromatography on silica using ethyl acetate/n-heptane (75/25) to elute unpolar impurities, followed by ethyl acetate to afford the title compound as a yellow solid (12.2 g, 32%).1H-NMR (400 MHz, CDCl3): δ=2.40 (s, 3H), 2.69 (t, 2H), 3.58-3.62 (m, 2H), 5.31 8br-s-, 1H), 6.58 (d, 1H), 7.97 (d, 1H)
Stage #1: <i>N</i>-(6-methyl-[2]pyridyl)-β-alanine With chlorosulfonic acid In dichloromethane at 20℃; for 2h; Cooling with ice; Stage #2: With sodium hydroxide In dichloromethane; water Stage #3: With sodium carbonate In dichloromethane; water 9.A To commercially available 2-amino-6-methylpyridine (25.46 g, 235 mmol) was added ethyl acrylate (26 mL, 239 mmol) and acetic acid (6 mL, 105 mmol). This mixture was heated at -150 °C in a sand bath for 50 h. The mixture was cooled to room temperature and 6 N sodium hydroxide (120 mL, 720 mmol) was added. The mixture was then heated at -120 °C in a sand bath for 1 h. The mixture was cooled to room temperature and concentrated hydrochloric acid was added until the pH reached approx. 4-5 with ice-cooling. A polymeric precipitate was formed and the mixture was filtered. The filtrate was evaporated and the residue was treated with methanol (100 mL). The resulting slurry was stirred at room temperature for 30 minutes and filtered. The precipitate was washed with methanol (30 mL) and the combined filtrates were evaporated to leave a brownish, sticky mass. This crude material was dissolved in dichloromethane (400 mL) and the solution was placed in an ice-bath. Then chlorosulibnic acid (162 mL, 2430 mmol) was added dropwise. After the addition was completed, the mixture was stirred at room temperature for 2 h. Then the mixture was placed back into the ice-bath and water (800 mL) was carefully added. After the addition was completed, the acidic solution was made alkaline to pH ~6 by adding sodium hydroxide. Then sodium carbonate was added to adjust the pH to -10 to 1 1. A precipitate was formed and the mixture was extracted with ethyl acetate (3 x 400 mL). The organic phase was separated, dried over Na2S04, filtered and the solvents were removed. The residue was purified by chromatography on silica using ethyl acetate/n-heptane (75/25) to elute unpolar impurities, followed by ethyl acetate to afford the title compound as a yellow solid ( 12.2 g, 32 %).-NMR (400 MHz, CDC13): d = 2.40 (s, 3H), 2.69 (t, 2H), 3.58-3.62 (m, 2H), 5.31 8br-s-, 1 H), 6.58 (d, 1 H), 7.97 (d, 1 H)
  • 43
  • [ 1824-81-3 ]
  • [ 140-88-5 ]
  • [ 55469-90-4 ]
YieldReaction ConditionsOperation in experiment
32% Stage #1: 2-Amino-6-methylpyridine; ethyl acrylate With acetic acid at 150℃; for 50h; Stage #2: With sodium hydroxide at 20 - 120℃; for 1h; 9.A Preparation Example 9 (compound 9): [Show Image] Step A; To commercially available 2-amino-6-methylpyridine (25.46 g, 235 mmol) was added ethyl acrylate (26 mL, 239 mmol) and acetic acid (6 mL, 105 mmol). This mixture was heated at ∼150 °C in a sand bath for 50 h. The mixture was cooled to room temperature and 6 N sodium hydroxide (120 mL, 720 mmol) was added. The mixture was then heated ant ∼120 °C in a sand bath for 1 h. The mixture was cooled to room temperature and concentrated hydrochloric acid was added until the pH reached approx. 4-5 with ice-cooling. A polymeric precipitate was formed and the mixture was filtered. The filtrate was evaporated and the residue was treated with methanol (100 mL). The resulting slurry was stirred at room temperature for 30 minutes and filtered. The precipitate was washed with methanol (30 mL) and the combined filtrates were evaporated to leave a brownish, sticky mass. This crude material was dissolved in dichloromethane (400 mL) and the solution was placed in an ice-bath. Then chlorosulfonic acid (162 mL, 2430 mmol) was added dropwise. After the addition was completed, the mixture was stirred at room temperature for 2 h. Then the mixture was placed back into the ice-bath and water (800 mL) was carefully added. After the addition was completed, the acidic solution was made alkaline to pH ∼6 by adding sodium hydroxide. Then sodium carbonate was added to adjust the pH to ∼10 to 11. A precipitate was formed and the mixture was extracted with ethyl acetate (3 x 400 mL). The organic phase was separated, dried over Na2SO4, filtered and the solvents were removed. The residue was purified by chromatography on silica using ethyl acetate/n-heptane (75/25) to elute unpolar impurities, followed by ethyl acetate to afford the title compound as a yellow solid (12.2 g, 32 %). 1H-NMR (400 MHz, CDCl3): d = 2.40 (s, 3H), 2.69 (t, 2H), 3.58-3.62 (m, 2H), 5.31 8br-s-. 1H), 6.58 (d, 1H), 7.97 (d, 1H)
  • 44
  • [ 55469-90-4 ]
  • methyl N-[(2,6-dichlorophenyl)carbonyl]-O-[2-(5-methyl-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl]-L-tyrosinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: dmap / tetrahydrofuran / 50 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -20 - -10 °C 2.2: 20 °C 3.1: hydrogen / palladium 10% on activated carbon / methanol / 2 h / 750.08 Torr 4.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 1.5 h / -60 °C 5.1: lithium borohydride / tetrahydrofuran / 20 °C 6.1: di-tert-butyl-diazodicarboxylate; triphenylphosphine / dichloromethane 7.1: trifluoroacetic acid / dichloromethane
  • 45
  • [ 55469-90-4 ]
  • N-[(2,6-dichlorophenyl)carbonyl]-O-[2-(5-methyl-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl]-L-tyrosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: dmap / tetrahydrofuran / 50 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -20 - -10 °C 2.2: 20 °C 3.1: hydrogen / palladium 10% on activated carbon / methanol / 2 h / 750.08 Torr 4.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 1.5 h / -60 °C 5.1: lithium borohydride / tetrahydrofuran / 20 °C 6.1: di-tert-butyl-diazodicarboxylate; triphenylphosphine / dichloromethane 7.1: trifluoroacetic acid / dichloromethane 8.1: lithium hydroxide; water / N,N-dimethyl-formamide / 18 h / 20 °C
  • 46
  • [ 55469-90-4 ]
  • [ 959992-93-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: dmap / tetrahydrofuran / 50 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -20 - -10 °C 2.2: 20 °C 3.1: hydrogen / palladium 10% on activated carbon / methanol / 2 h / 750.08 Torr
  • 47
  • [ 55469-90-4 ]
  • [ 959992-92-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: dmap / tetrahydrofuran / 50 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -20 - -10 °C 2.2: 20 °C
  • 48
  • [ 55469-90-4 ]
  • [ 959992-90-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: dmap / tetrahydrofuran / 50 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -20 - -10 °C 2.2: 20 °C 3.1: hydrogen / palladium 10% on activated carbon / methanol / 2 h / 750.08 Torr 4.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 1.5 h / -60 °C 5.1: lithium borohydride / tetrahydrofuran / 20 °C
  • 49
  • [ 55469-90-4 ]
  • [ 959992-94-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: dmap / tetrahydrofuran / 50 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -20 - -10 °C 2.2: 20 °C 3.1: hydrogen / palladium 10% on activated carbon / methanol / 2 h / 750.08 Torr 4.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 1.5 h / -60 °C
  • 50
  • [ 55469-90-4 ]
  • C33H37Cl2N3O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: dmap / tetrahydrofuran / 50 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -20 - -10 °C 2.2: 20 °C 3.1: hydrogen / palladium 10% on activated carbon / methanol / 2 h / 750.08 Torr 4.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 1.5 h / -60 °C 5.1: lithium borohydride / tetrahydrofuran / 20 °C 6.1: di-tert-butyl-diazodicarboxylate; triphenylphosphine / dichloromethane
Same Skeleton Products
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