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inquiry6-(4-Chlorophenyl)-2,3-Dihydro-2,2-Dimethyl-7-phenyl-1H-Pyrrolizine Application:6-(4-Chlorophenyl)-2,3-Dihydro-2,2-Dimethyl-7-phenyl-1H-Pyrrolizine
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inquiry4-chlorobenzoylmethyl bromide
5-benzyl-3,3-dimethyl-3,4-dihydro-2H-pyrrole
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine
Conditions | Yield |
---|---|
Stage #1: 5-benzyl-3,3-dimethyl-3,4-dihydro-2H-pyrrole With sodium hydrogencarbonate In methanol Stage #2: 4-chlorobenzoylmethyl bromide In methanol for 20h; Stage #3: With water at 40℃; for 1h; | 84% |
With sodium hydrogencarbonate In ethanol at 20℃; for 36h; | 25% |
With sodium hydrogencarbonate In ethanol; water at 20℃; for 36h; | 25% |
4-Chlorophenylboronic acid
2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-6-yl trifluoromethanesulfonate
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine
Conditions | Yield |
---|---|
With potassium hydroxide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran 1) rt, overnight; 2) reflux, 24 h; | 15% |
(4-chlorphenyl)magnesium bromide
N,N-diethyl 2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-6-yl carbamate
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine
Conditions | Yield |
---|---|
With Ni(aca)2 In tetrahydrofuran Heating; Yield given; |
(4-chlorphenyl)magnesium bromide
diethyl 2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-6-yl phosphate
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine
Conditions | Yield |
---|---|
With Ni(aca)2 In tetrahydrofuran Heating; Yield given; |
1-chloro-3-phenyl-2-propyne
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine
Conditions | Yield |
---|---|
Multi-step reaction with 5 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: 1.) NaH / 1) THF, rt, 1 h; 2) THF, 0 deg C, 5 min, rt, 20 h 5: 15 percent / Pd(PPh3)4, aq. KOH / tetrahydrofuran / 1) rt, overnight; 2) reflux, 24 h View Scheme | |
Multi-step reaction with 5 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: 1.) NaH / 1) THF, rt, 1 h; 2) THF, 0 deg C, 5 min, rt, 20 h 5: Ni(aca)2 / tetrahydrofuran / Heating View Scheme | |
Multi-step reaction with 5 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: 1.) NaH / 1) THF, rt, 1 h; 2) THF, 0 deg C, 5 min, rt, 20 h 5: Ni(aca)2 / tetrahydrofuran / Heating View Scheme |
2,2-dimethyl-5-phenylpent-4-ynal
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine
Conditions | Yield |
---|---|
Multi-step reaction with 4 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: 1.) NaH / 1) THF, rt, 1 h; 2) THF, 0 deg C, 5 min, rt, 20 h 4: 15 percent / Pd(PPh3)4, aq. KOH / tetrahydrofuran / 1) rt, overnight; 2) reflux, 24 h View Scheme | |
Multi-step reaction with 4 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: 1.) NaH / 1) THF, rt, 1 h; 2) THF, 0 deg C, 5 min, rt, 20 h 4: Ni(aca)2 / tetrahydrofuran / Heating View Scheme | |
Multi-step reaction with 4 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: 1.) NaH / 1) THF, rt, 1 h; 2) THF, 0 deg C, 5 min, rt, 20 h 4: Ni(aca)2 / tetrahydrofuran / Heating View Scheme |
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine
Conditions | Yield |
---|---|
Stage #1: 6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine With dipotassium peroxodisulfate; acetic acid; [2,2]bipyridinyl; palladium diacetate at 20 - 100℃; for 8h; Stage #2: With sodium carbonate In water pH=7; | 88% |
methanol
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine
trichloromethyl chloroformate
6-(4-chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-1H-pyrrolizine-5-carboxylic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: 6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine; trichloromethyl chloroformate With triethylamine In tetrahydrofuran at 20℃; for 7h; Stage #2: methanol In tetrahydrofuran at 20℃; for 12h; | 84% |
methyl 2-iodoacetate
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine
methyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl)acetate
Conditions | Yield |
---|---|
With dihydrogen peroxide; iron(II) sulfate; dimethyl sulfoxide In water at 10 - 20℃; for 0.25h; Product distribution / selectivity; Cooling with cold water bath; | 78% |
With dihydrogen peroxide; iron(II) sulfate; dimethyl sulfoxide; sodium iodide at 10 - 20℃; for 0.333333h; Product distribution / selectivity; Cooling with cold water bath; | 45% |
With dihydrogen peroxide; iron(II) sulfate In dimethyl sulfoxide for 1h; |
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine
ethyl iodoacetae
ethyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetate
Conditions | Yield |
---|---|
With dihydrogen peroxide; iron(II) sulfate In dimethyl sulfoxide for 1h; | 78% |
With dihydrogen peroxide; iron(II) sulfate; dimethyl sulfoxide In water; acetonitrile at 5 - 18℃; for 0.25h; Product distribution / selectivity; Cooling with cold water bath; | 59% |
With dihydrogen peroxide; iron(II) sulfate; dimethyl sulfoxide In water at 10 - 20℃; for 0.25 - 2h; Product distribution / selectivity; Cooling with cold water bath; | 51% |
ethyl bromoacetate
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine
ethyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetate
Conditions | Yield |
---|---|
With dihydrogen peroxide; iron(II) sulfate; sodium iodide In dimethyl sulfoxide for 1h; | 75% |
propionic acid anhydride
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine
1-(2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl)propan-1-one
Conditions | Yield |
---|---|
With aluminum (III) chloride In diethyl ether at 20℃; Inert atmosphere; | 73.2% |
hexyl iodoacetate
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine
Conditions | Yield |
---|---|
With dihydrogen peroxide; iron(II) sulfate; dimethyl sulfoxide In water at 10 - 20℃; for 0.25h; Product distribution / selectivity; Cooling with cold water bath; | 73% |
iodoacetonitrile
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine
2-[6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl]acetonitrile
Conditions | Yield |
---|---|
With dihydrogen peroxide; iron(II) sulfate In dimethyl sulfoxide for 4.5h; | 65% |
With dihydrogen peroxide; iron(II) sulfate; dimethyl sulfoxide In water at 10 - 20℃; for 0.25h; Product distribution / selectivity; Cooling with cold water bath; | 65% |
bromoacetic acid tert-butyl ester
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine
[6-(4-chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-1H-pyrrolizin-5-yl]acetic acid tert-butyl ester
Conditions | Yield |
---|---|
With dihydrogen peroxide; iron(II) sulfate; sodium iodide In dimethyl sulfoxide; acetonitrile for 10h; | 62% |
t-butyl iodoacetate
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine
[6-(4-chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-1H-pyrrolizin-5-yl]acetic acid tert-butyl ester
Conditions | Yield |
---|---|
With dihydrogen peroxide; iron(II) sulfate; dimethyl sulfoxide In water at 10 - 20℃; for 0.25 - 1.83333h; Product distribution / selectivity; Cooling with cold water bath; | 60% |
With dihydrogen peroxide; iron(II) sulfate In dimethyl sulfoxide for 10h; |
chloroacetyl chloride
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine
2-chloro-1-(2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl)ethanone
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In diethyl ether at 20℃; Inert atmosphere; | 59.3% |
With boron trifluoride diethyl etherate at 20℃; for 3h; Inert atmosphere; | 59% |
bromoacetic acid methyl ester
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine
methyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl)acetate
Conditions | Yield |
---|---|
With dihydrogen peroxide; iron(II) sulfate; sodium iodide In dimethyl sulfoxide for 1h; | 57% |
n-hexanoic anhydride
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine
1-(2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl)hexan-1-one
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In diethyl ether at 20℃; Inert atmosphere; | 56.3% |
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine
dibenzoyl peroxide
Conditions | Yield |
---|---|
Stage #1: 6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine With tert.-butyl lithium In diethyl ether; pentane at -70 - 20℃; for 3h; Stage #2: dibenzoyl peroxide In diethyl ether; pentane at -70 - 20℃; for 16 - 29h; | 53% |
acetic anhydride
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine
1-(2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl)ethanone
Conditions | Yield |
---|---|
With aluminum (III) chloride In diethyl ether at 20℃; Inert atmosphere; | 43.2% |
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine
Conditions | Yield |
---|---|
With copper In tetrahydrofuran for 1h; Heating; | 26.5% |
diazoacetic acid ethyl ester
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine
ethyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetate
Conditions | Yield |
---|---|
With copper In toluene for 0.25h; Heating; |
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 |
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; |
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine
Conditions | Yield |
---|---|
With dihydrogen peroxide; iron(II); dimethyl sulfoxide |
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