6-(4-Chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-1H-pyrrolizine supplier

Name
6-(4-Chlorophenyl)-2,3-Dihydro-2,2-DiMethyl-7-Phenyl-1H-Pyrrolizine
EINECS
CAS No. 133111-56-5
Article Data9
CAS DataBase
Density
Solubility
Melting Point
Formula C21H20 Cl N
Boiling Point
Molecular Weight 321.85
Flash Point
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 6-(4-Chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine
PSA 4.93000
LogP 6.05780

Synthetic route

: 536-38-9
4-chlorobenzoylmethyl bromide

: 116673-95-1
5-benzyl-3,3-dimethyl-3,4-dihydro-2H-pyrrole

: 133111-56-5
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine

Conditions

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%

: 1679-18-1
4-Chlorophenylboronic acid

: 226900-28-3
2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-6-yl trifluoromethanesulfonate

: 133111-56-5
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine

Conditions

Conditions	Yield
With potassium hydroxide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran 1) rt, overnight; 2) reflux, 24 h;	15%

: 873-77-8
(4-chlorphenyl)magnesium bromide

: 226900-31-8
N,N-diethyl 2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-6-yl carbamate

: 133111-56-5
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine

Conditions

Conditions	Yield
With Ni(aca)2 In tetrahydrofuran Heating; Yield given;

: 873-77-8
(4-chlorphenyl)magnesium bromide

: 226900-35-2
diethyl 2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-6-yl phosphate

: 133111-56-5
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine

Conditions

Conditions	Yield
With Ni(aca)2 In tetrahydrofuran Heating; Yield given;

: 3355-31-5
1-chloro-3-phenyl-2-propyne

(1,2-dimethyl-3-zirconacyclopent-1-ene)(C5H5)2: (1,2-dimethyl-3-zirconacyclopent-1-ene)(C5H5)2

: 133111-56-5
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine

Conditions

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

: 197963-29-4
2,2-dimethyl-5-phenylpent-4-ynal

: 133111-56-5
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine

Conditions

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

: 133111-56-5
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine

: 2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-5,6-dihydro-pyrrolizin-3-one

Conditions

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%

: 67-56-1
methanol

: 133111-56-5
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine

: 503-38-8
trichloromethyl chloroformate

: 262426-69-7
6-(4-chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-1H-pyrrolizine-5-carboxylic acid methyl ester

Conditions

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%

...Expand

: 5199-50-8
methyl 2-iodoacetate

: 133111-56-5
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine

: 1061179-20-1
methyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl)acetate

Conditions

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;

: 133111-56-5
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine

: 623-48-3
ethyl iodoacetae

: 156897-35-7
ethyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetate

Conditions

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%

: 105-36-2
ethyl bromoacetate

: 133111-56-5
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine

: 156897-35-7
ethyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetate

Conditions

Conditions	Yield
With dihydrogen peroxide; iron(II) sulfate; sodium iodide In dimethyl sulfoxide for 1h;	75%

: 123-62-6
propionic acid anhydride

: 133111-56-5
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine

: 1281816-31-6
1-(2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl)propan-1-one

Conditions

Conditions	Yield
With aluminum (III) chloride In diethyl ether at 20℃; Inert atmosphere;	73.2%

: 5436-99-7
hexyl iodoacetate

: 133111-56-5
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine

: hexyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl)acetate

Conditions

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%

: 624-75-9
iodoacetonitrile

: 133111-56-5
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine

: 1061179-18-7
2-[6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl]acetonitrile

Conditions

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%

: 5292-43-3
bromoacetic acid tert-butyl ester

: 133111-56-5
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine

: 262426-70-0
[6-(4-chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-1H-pyrrolizin-5-yl]acetic acid tert-butyl ester

Conditions

Conditions	Yield
With dihydrogen peroxide; iron(II) sulfate; sodium iodide In dimethyl sulfoxide; acetonitrile for 10h;	62%

: 49827-15-8
t-butyl iodoacetate

: 133111-56-5
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine

: 262426-70-0
[6-(4-chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-1H-pyrrolizin-5-yl]acetic acid tert-butyl ester

Conditions

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;

: 79-04-9
chloroacetyl chloride

: 133111-56-5
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine

: 1281816-34-9
2-chloro-1-(2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl)ethanone

Conditions

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%

: 96-32-2
bromoacetic acid methyl ester

: 133111-56-5
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine

: 1061179-20-1
methyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl)acetate

Conditions

Conditions	Yield
With dihydrogen peroxide; iron(II) sulfate; sodium iodide In dimethyl sulfoxide for 1h;	57%

: 2051-49-2
n-hexanoic anhydride

: 133111-56-5
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine

: 1281816-32-7
1-(2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl)hexan-1-one

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In diethyl ether at 20℃; Inert atmosphere;	56.3%

: 133111-56-5
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine

: 94-36-0
dibenzoyl peroxide

: benzoic acid [2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl] ester

Conditions

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%

: 108-24-7
acetic anhydride

: 133111-56-5
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine

: 1281816-29-2
1-(2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl)ethanone

Conditions

Conditions	Yield
With aluminum (III) chloride In diethyl ether at 20℃; Inert atmosphere;	43.2%

: 133111-56-5
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine

: diazo-<2-(14)C>-acetic acid ethylester

: C24(14)CH26ClNO2

Conditions

Conditions	Yield
With copper In tetrahydrofuran for 1h; Heating;	26.5%

: 623-73-4
diazoacetic acid ethyl ester

: 133111-56-5
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine

: 156897-35-7
ethyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetate

Conditions

Conditions	Yield
With copper In toluene for 0.25h; Heating;

: 133111-56-5
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine

: 156897-06-2
licofelone

Conditions

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

: 79-37-8
oxalyl dichloride

: 133111-56-5
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine

: 156897-06-2
licofelone

Conditions

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;

Reaxys ID: 19180192: Reaxys ID: 19180192

: 133111-56-5
2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine

Reaxys ID: 19180191: Reaxys ID: 19180191

Conditions

Conditions	Yield
With dihydrogen peroxide; iron(II); dimethyl sulfoxide

6-(4-Chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-1H-pyrrolizine Chemical Properties

Molecule structure of 6-(4-Chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-1H-pyrrolizine (CAS NO.133111-56-5):

Molecular Weight: 321.843 g/mol
Molecular Formula: C₂₁H₂₀ClN
Smiles of 6-(4-Chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-1H-pyrrolizine (CAS NO.133111-56-5): CC1(C)CC2=C(c3ccccc3)C(c4ccc(Cl)cc4)=CN2C1

Product Name

6-(4-Chlorophenyl)-2,3-Dihydro-2,2-DiMethyl-7-Phenyl-1H-Pyrrolizine

Synthetic route

6-(4-Chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-1H-pyrrolizine Chemical Properties

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