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inquiryethyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetate
licofelone
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water at 80℃; | 77% |
With sodium hydroxide In ethanol at 80℃; for 0.25h; | 77% |
With sodium hydroxide In ethanol for 0.166667h; Heating; | 75.5% |
Stage #1: ethyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetate With sodium hydroxide; water In ethanol for 0.5h; Heating / reflux; Stage #2: With hydrogenchloride In ethanol; water Product distribution / selectivity; | 64% |
With aq. alkaline hydroxide at 60 - 70℃; for 1h; |
methyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl)acetate
licofelone
Conditions | Yield |
---|---|
Stage #1: methyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl)acetate With sodium hydroxide; water In ethanol for 0.5h; Heating / reflux; Stage #2: With hydrogenchloride In ethanol; water Product distribution / selectivity; | 71% |
With aq. alkaline hydroxide at 60 - 70℃; for 1h; |
[6-(4-chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-1H-pyrrolizin-5-yl]acetic acid tert-butyl ester
licofelone
Conditions | Yield |
---|---|
Stage #1: [6-(4-chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-1H-pyrrolizin-5-yl]acetic acid tert-butyl ester With sodium hydroxide; water In ethanol for 8h; Heating / reflux; Stage #2: With hydrogenchloride In ethanol; water Product distribution / selectivity; | 60% |
With aq. alkaline hydroxide at 60 - 70℃; for 10h; |
licofelone
Conditions | Yield |
---|---|
With hydrazine hydrate; potassium hydroxide In ethylene diglycol at 85 - 145℃; for 7h; Wolff-Kishner reduction; | 55% |
With hydrazine hydrate; potassium hydroxide In diethylene glycol at 85 - 145℃; for 7h; Wolff-Kishner reduction; | 55% |
With hydrazine hydrate; potassium hydroxide In diethylene glycol at 50 - 145℃; Wolff-Kishner reduction; | 55.6% |
2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl)acetamide
licofelone
Conditions | Yield |
---|---|
Stage #1: 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl)acetamide With sulfuric acid; water In methanol for 4h; Heating / reflux; Stage #2: With sodium hydroxide; water In methanol for 4h; Heating / reflux; Stage #3: With hydrogenchloride In methanol; water Product distribution / selectivity; | 50% |
1-chloro-3-phenyl-2-propyne
licofelone
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 90 percent / aq. NaOH, NaI, n-Bu4NI / toluene / 24 h / 50 °C 2: 1.) Et3N, 2.) NaBH(OAc)3 / 1) CH2Cl2, rt, 15 min; 2) CH2Cl2, rt, 12 h 3: 68 percent / pivalic acid / 5 h / 150 °C 4: 77 percent / EtONa / ethanol / 15 h / Ambient temperature 5: 1.) NaH / 1) THF, rt, 1 h; 2) THF, rt, 12 h 6: 92 percent / Pd(PPh3)4, Na2CO3 / tetrahydrofuran; H2O / 1) rt, 1 h; 2) reflux, 1 h 7: 1.) p-toluenesulfonhydrazide, p-TsOH*H2O, 2.) NaBH3CN / 1) EtOH, reflux, 7 h; 2) EtOH, reflux, 4 h 8: 77 percent / aq. NaOH / ethanol / 0.25 h / 80 °C View Scheme |
2,2-dimethyl-5-phenylpent-4-ynal
licofelone
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 1.) Et3N, 2.) NaBH(OAc)3 / 1) CH2Cl2, rt, 15 min; 2) CH2Cl2, rt, 12 h 2: 68 percent / pivalic acid / 5 h / 150 °C 3: 77 percent / EtONa / ethanol / 15 h / Ambient temperature 4: 1.) NaH / 1) THF, rt, 1 h; 2) THF, rt, 12 h 5: 92 percent / Pd(PPh3)4, Na2CO3 / tetrahydrofuran; H2O / 1) rt, 1 h; 2) reflux, 1 h 6: 1.) p-toluenesulfonhydrazide, p-TsOH*H2O, 2.) NaBH3CN / 1) EtOH, reflux, 7 h; 2) EtOH, reflux, 4 h 7: 77 percent / aq. NaOH / ethanol / 0.25 h / 80 °C View Scheme | |
Multi-step reaction with 7 steps 1: 80 percent / NaBH(OAc)3, Et3N / CH2Cl2 / Ambient temperature 2: 68 percent / t-BuCO2H / 150 °C 3: 77 percent / EtONa / ethanol / Ambient temperature 4: 80 percent / NaH / tetrahydrofuran / Ambient temperature 5: 92 percent / Pd(PPh3)4, Na2CO3 / H2O; tetrahydrofuran / Heating 6: 1.) p-toluenesulfonyl hydrazide, p-TsOH, 2.) NaBH3CN / 1.) EtOH, reflux, 2.) EtOH, reflux 7: 77 percent / NaOH / ethanol; H2O / 80 °C View Scheme |
2,2-dimethyl-7-phenyl-2,3,5,6-tetrahydro-1H-pyrrolizin-6-one
licofelone
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 77 percent / EtONa / ethanol / 15 h / Ambient temperature 2: 1.) NaH / 1) THF, rt, 1 h; 2) THF, rt, 12 h 3: 92 percent / Pd(PPh3)4, Na2CO3 / tetrahydrofuran; H2O / 1) rt, 1 h; 2) reflux, 1 h 4: 1.) p-toluenesulfonhydrazide, p-TsOH*H2O, 2.) NaBH3CN / 1) EtOH, reflux, 7 h; 2) EtOH, reflux, 4 h 5: 77 percent / aq. NaOH / ethanol / 0.25 h / 80 °C View Scheme | |
Multi-step reaction with 5 steps 1: 77 percent / EtONa / ethanol / Ambient temperature 2: 80 percent / NaH / tetrahydrofuran / Ambient temperature 3: 92 percent / Pd(PPh3)4, Na2CO3 / H2O; tetrahydrofuran / Heating 4: 1.) p-toluenesulfonyl hydrazide, p-TsOH, 2.) NaBH3CN / 1.) EtOH, reflux, 2.) EtOH, reflux 5: 77 percent / NaOH / ethanol; H2O / 80 °C View Scheme |
methyl N-(2,2-dimethyl-5-phenylpent-4-ynyl)glycinate
licofelone
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 68 percent / pivalic acid / 5 h / 150 °C 2: 77 percent / EtONa / ethanol / 15 h / Ambient temperature 3: 1.) NaH / 1) THF, rt, 1 h; 2) THF, rt, 12 h 4: 92 percent / Pd(PPh3)4, Na2CO3 / tetrahydrofuran; H2O / 1) rt, 1 h; 2) reflux, 1 h 5: 1.) p-toluenesulfonhydrazide, p-TsOH*H2O, 2.) NaBH3CN / 1) EtOH, reflux, 7 h; 2) EtOH, reflux, 4 h 6: 77 percent / aq. NaOH / ethanol / 0.25 h / 80 °C View Scheme | |
Multi-step reaction with 6 steps 1: 68 percent / t-BuCO2H / 150 °C 2: 77 percent / EtONa / ethanol / Ambient temperature 3: 80 percent / NaH / tetrahydrofuran / Ambient temperature 4: 92 percent / Pd(PPh3)4, Na2CO3 / H2O; tetrahydrofuran / Heating 5: 1.) p-toluenesulfonyl hydrazide, p-TsOH, 2.) NaBH3CN / 1.) EtOH, reflux, 2.) EtOH, reflux 6: 77 percent / NaOH / ethanol; H2O / 80 °C View Scheme |
ethyl 2-(2,2-dimethyl-6-hydroxy-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)-2-oxoacetate
licofelone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 1.) NaH / 1) THF, rt, 1 h; 2) THF, rt, 12 h 2: 92 percent / Pd(PPh3)4, Na2CO3 / tetrahydrofuran; H2O / 1) rt, 1 h; 2) reflux, 1 h 3: 1.) p-toluenesulfonhydrazide, p-TsOH*H2O, 2.) NaBH3CN / 1) EtOH, reflux, 7 h; 2) EtOH, reflux, 4 h 4: 77 percent / aq. NaOH / ethanol / 0.25 h / 80 °C View Scheme | |
Multi-step reaction with 4 steps 1: 80 percent / NaH / tetrahydrofuran / Ambient temperature 2: 92 percent / Pd(PPh3)4, Na2CO3 / H2O; tetrahydrofuran / Heating 3: 1.) p-toluenesulfonyl hydrazide, p-TsOH, 2.) NaBH3CN / 1.) EtOH, reflux, 2.) EtOH, reflux 4: 77 percent / NaOH / ethanol; H2O / 80 °C View Scheme |
ethyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)-2-oxoacetate
licofelone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) p-toluenesulfonhydrazide, p-TsOH*H2O, 2.) NaBH3CN / 1) EtOH, reflux, 7 h; 2) EtOH, reflux, 4 h 2: 77 percent / aq. NaOH / ethanol / 0.25 h / 80 °C View Scheme | |
Multi-step reaction with 2 steps 1: 1.) p-toluenesulfonyl hydrazide, p-TsOH, 2.) NaBH3CN / 1.) EtOH, reflux, 2.) EtOH, reflux 2: 77 percent / NaOH / ethanol; H2O / 80 °C View Scheme |
ethyl 2-(2,2-dimethyl-7-phenyl-6-trifluoromethanesulfonyloxy-2,3-dihydro-1H-pyrrolizin-5-yl)-2-oxoacetate
licofelone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 92 percent / Pd(PPh3)4, Na2CO3 / tetrahydrofuran; H2O / 1) rt, 1 h; 2) reflux, 1 h 2: 1.) p-toluenesulfonhydrazide, p-TsOH*H2O, 2.) NaBH3CN / 1) EtOH, reflux, 7 h; 2) EtOH, reflux, 4 h 3: 77 percent / aq. NaOH / ethanol / 0.25 h / 80 °C View Scheme | |
Multi-step reaction with 3 steps 1: 92 percent / Pd(PPh3)4, Na2CO3 / H2O; tetrahydrofuran / Heating 2: 1.) p-toluenesulfonyl hydrazide, p-TsOH, 2.) NaBH3CN / 1.) EtOH, reflux, 2.) EtOH, reflux 3: 77 percent / NaOH / ethanol; H2O / 80 °C View Scheme |
1-chloro-3-phenyl-2-propyne
licofelone
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 90 percent / n-Bu4NI, NaI, NaOH / H2O; toluene / 50 °C 2: 80 percent / NaBH(OAc)3, Et3N / CH2Cl2 / Ambient temperature 3: 68 percent / t-BuCO2H / 150 °C 4: 77 percent / EtONa / ethanol / Ambient temperature 5: 80 percent / NaH / tetrahydrofuran / Ambient temperature 6: 92 percent / Pd(PPh3)4, Na2CO3 / H2O; tetrahydrofuran / Heating 7: 1.) p-toluenesulfonyl hydrazide, p-TsOH, 2.) NaBH3CN / 1.) EtOH, reflux, 2.) EtOH, reflux 8: 77 percent / NaOH / ethanol; H2O / 80 °C View Scheme |
4-chlorobenzoylmethyl bromide
licofelone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: NaHCO3 / diethyl ether; ethanol; H2O / 36 h / Ambient temperature 2: Cu / toluene / 0.25 h / Heating 3: 75.5 percent / 10percent aq. NaOH / ethanol / 0.17 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1.1: ethanol / 0.5 h 2.1: tetrahydrofuran / 18 - 25 °C / Inert atmosphere 2.2: 0.33 h / 25 - 30 °C 3.1: hydrazine hydrate; potassium hydroxide / diethylene glycol / 50 - 145 °C View Scheme |
5-benzyl-3,3-dimethyl-3,4-dihydro-2H-pyrrole
licofelone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: NaHCO3 / diethyl ether; ethanol; H2O / 36 h / Ambient temperature 2: Cu / toluene / 0.25 h / Heating 3: 75.5 percent / 10percent aq. NaOH / ethanol / 0.17 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium hydrogencarbonate / ethanol / 36 h / 20 °C 2.1: tetrahydrofuran / 10 - 15 °C 2.2: 0.33 h / 25 - 30 °C 3.1: hydrazine hydrate; potassium hydroxide / ethylene diglycol / 7 h / 85 - 145 °C View Scheme | |
Multi-step reaction with 4 steps 1: sodium hydrogencarbonate / ethanol; water / 36 h / 20 °C 2: tetrahydrofuran / 10 - 15 °C 3: water / tetrahydrofuran / 0.33 h / 25 - 30 °C 4: hydrazine hydrate; potassium hydroxide / diethylene glycol / 7 h / 85 - 145 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: ethanol / 0.5 h 2.1: tetrahydrofuran / 18 - 25 °C / Inert atmosphere 2.2: 0.33 h / 25 - 30 °C 3.1: hydrazine hydrate; potassium hydroxide / diethylene glycol / 50 - 145 °C View Scheme |
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine
licofelone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Cu / toluene / 0.25 h / Heating 2: 75.5 percent / 10percent aq. NaOH / ethanol / 0.17 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 10 - 15 °C 1.2: 0.33 h / 25 - 30 °C 2.1: hydrazine hydrate; potassium hydroxide / ethylene diglycol / 7 h / 85 - 145 °C View Scheme | |
Multi-step reaction with 3 steps 1: tetrahydrofuran / 10 - 15 °C 2: water / tetrahydrofuran / 0.33 h / 25 - 30 °C 3: hydrazine hydrate; potassium hydroxide / diethylene glycol / 7 h / 85 - 145 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 18 - 25 °C / Inert atmosphere 1.2: 0.33 h / 25 - 30 °C 2.1: hydrazine hydrate; potassium hydroxide / diethylene glycol / 50 - 145 °C View Scheme |
licofelone
Conditions | Yield |
---|---|
In methanol; ethyl acetate at 0 - 5℃; for 5h; |
oxalyl dichloride
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine
licofelone
Conditions | Yield |
---|---|
Stage #1: oxalyl dichloride; 6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine In tetrahydrofuran at 10 - 25℃; for 0.5 - 0.75h; Stage #2: With water In tetrahydrofuran at 0 - 30℃; for 0.0833333 - 0.166667h; Stage #3: With hydrogenchloride; potassium hydroxide; hydrazine more than 3 stages; |
5.5-dimethyl-1,3,2-dioxathiane-2-oxide
licofelone
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: dimethyl sulfoxide / 36 h / 100 °C 2.1: pyridine; thionyl chloride / 0 °C 3.1: diethyl ether / 2 h / Reflux 3.2: 3 h / Reflux 4.1: sodium hydrogencarbonate / ethanol / 36 h / 20 °C 5.1: tetrahydrofuran / 10 - 15 °C 5.2: 0.33 h / 25 - 30 °C 6.1: hydrazine hydrate; potassium hydroxide / ethylene diglycol / 7 h / 85 - 145 °C View Scheme |
3,3-dimethyl-4-hydroxy butyronitrile
licofelone
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: pyridine; thionyl chloride / 0 °C 2.1: diethyl ether / 2 h / Reflux 2.2: 3 h / Reflux 3.1: sodium hydrogencarbonate / ethanol / 36 h / 20 °C 4.1: tetrahydrofuran / 10 - 15 °C 4.2: 0.33 h / 25 - 30 °C 5.1: hydrazine hydrate; potassium hydroxide / ethylene diglycol / 7 h / 85 - 145 °C View Scheme |
2,2-Dimethyl-1,3-propanediol
licofelone
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: thionyl chloride / dichloromethane / 5 - 10 °C 2.1: dimethyl sulfoxide / 36 h / 100 °C 3.1: pyridine; thionyl chloride / 0 °C 4.1: diethyl ether / 2 h / Reflux 4.2: 3 h / Reflux 5.1: sodium hydrogencarbonate / ethanol / 36 h / 20 °C 6.1: tetrahydrofuran / 10 - 15 °C 6.2: 0.33 h / 25 - 30 °C 7.1: hydrazine hydrate; potassium hydroxide / ethylene diglycol / 7 h / 85 - 145 °C View Scheme |
4-chloro-3,3-dimethylbutyronitrile
licofelone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: diethyl ether / 2 h / Reflux 1.2: 3 h / Reflux 2.1: sodium hydrogencarbonate / ethanol / 36 h / 20 °C 3.1: tetrahydrofuran / 10 - 15 °C 3.2: 0.33 h / 25 - 30 °C 4.1: hydrazine hydrate; potassium hydroxide / ethylene diglycol / 7 h / 85 - 145 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: magnesium 1.2: 5 h / Reflux 2.1: sodium hydrogencarbonate / ethanol; water / 36 h / 20 °C 3.1: tetrahydrofuran / 10 - 15 °C 4.1: water / tetrahydrofuran / 0.33 h / 25 - 30 °C 5.1: hydrazine hydrate; potassium hydroxide / diethylene glycol / 7 h / 85 - 145 °C View Scheme |
C23H19Cl2NO2
licofelone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: water / tetrahydrofuran / 0.33 h / 25 - 30 °C 2: hydrazine hydrate; potassium hydroxide / diethylene glycol / 7 h / 85 - 145 °C View Scheme |
benzyl chloride
licofelone
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: magnesium 1.2: 5 h / Reflux 2.1: sodium hydrogencarbonate / ethanol; water / 36 h / 20 °C 3.1: tetrahydrofuran / 10 - 15 °C 4.1: water / tetrahydrofuran / 0.33 h / 25 - 30 °C 5.1: hydrazine hydrate; potassium hydroxide / diethylene glycol / 7 h / 85 - 145 °C View Scheme |
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; | 100% |
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; |
licofelone
1,1'-carbonyldiimidazole
2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)-1-(1H-imidazol-1-yl)ethanone
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 24h; | 97% |
In tetrahydrofuran at 20℃; for 0.5h; |
licofelone
2-amino-2-hydroxymethyl-1,3-propanediol
Conditions | Yield |
---|---|
In ethanol at 47℃; Industry scale; | 92% |
cholin hydroxide
licofelone
6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-ylacetic acid choline salt
Conditions | Yield |
---|---|
In ethanol; water at 75 - 77℃; Product distribution / selectivity; Industry scale; | 87% |
licofelone
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at -50 - 20℃; for 2h; | 72% |
1,8-diiodooctane
licofelone
8-iodooctyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetate
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 56℃; | 70.1% |
toluene
licofelone
Conditions | Yield |
---|---|
In diethyl ether at 60℃; | 70% |
1,3-dibromo-propane
licofelone
3-bromopropyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetate
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 56℃; | 68.7% |
ethylene dibromide
licofelone
2-bromoethyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetate
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 56℃; | 60.3% |
1,4-dibromo-butane
licofelone
4-bromobutyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetate
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 56℃; | 56.9% |
1,12-dibromododecane
licofelone
12-bromododecyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetate
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 56℃; | 43.1% |
licofelone
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In diethyl ether at 20℃; for 0.5h; | 1.3% |
toluene
licofelone
Conditions | Yield |
---|---|
In ethyl acetate at 40 - 50℃; |
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