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123-75-1 Usage

Chemical Properties

Pyrrolidine is acolourless to pale yellow liquid with a penetrating, It is infinitely miscible with water and conventional organic solvents such as methanol, acetone, ether, and chloroform. It acts as a lachrymator.Chemically, pyrrolidine behaves like a secondary amine in every respect. For example, it undergoes Leuckart – Wallach and Mannich reactions and is readily converted into an enamine. In the presence of a catalyst, such as platinum at 360°C or rhodium at 650°C, pyrrole is formed. In the presence of a copper catalyst, N-methylpyrrolidone is converted into Nmethylpyrrolidine.

Physical properties

Pyrrolidine has a penetrating amine-type odor, reminiscent of ammonia and piperidine. It is easy to turn yellow when exposed to light or humid air, easily soluble in water and ethanol. It is nauseating and diffusive.

Occurrence

Reported found in beer, bread, wheat bread, salmon caviar, fish, milk, leaves and stalks of celery, Camembert cheese, Limburger cheese, Russian cheeses, tilsit cheese, other cheeses, caviar, raw fatty fish, beer, Finnish whiskey, white wine, red wine, coffee, radish, malt, roasted peanut, sweet corn and roasted barley.

Uses

Pyrrolidine is a flammable alkaline liquid that undergoes reactions typical of secondary amines. It is used to prepare pesticides and rubber accelerators and as a chemical intermediate (usually the hydrochloride form) in the pharmaceutical industry. There is relatively limited industrial exposure to this material.

Application

Pyrrolidine is a heterocyclic compound used as a building block in the synthesis of wide range of pharmaceutical compounds, namely matrix metalloprotein inhibitors (MMPIs) and aminopeptidase N inhibitors (APNIs). It has been used for the synthesis of N-benzoyl pyrrolidine from benzaldehyde via oxidative amination. It may be used as a catalyst for the synthesis of N-sulfinyl aldimines from carbonyl compounds and sulfonamides.Pyrrolidine can also be used to synthesize:Taddol-pyrrolidine phosphoramidite, a ligand for rhodium-catalyzed [2+2+2] cycloaddition of pentenyl isocyanate and 4- ethynylanisole.H,4 PyrrolidineQuin-BAM (′PBAM′), a selective catalyst for the aza-Henry addition of nitroalkanes to aryl aldimines.1,2,3,3a,4,9-Hexahydropyrrolo[2,1-b]quinazoline by reacting with o-aminobenzaldehyde.

Preparation

Pyrrolidine is formed by reduction of pyrrole. Via overall 5-endo-trig cyclizations of homoallylic tosylamides. Pyrrolidine can be produced from butanediol and ammonia, e.g., over an aluminum thorium oxide catalyst at 300°C or over a nickel catalyst at 200°C and 20 MPa under hydrogenation conditions. It can also be produced from THF and ammonia over aluminum oxide at 275-375°C.

Definition

ChEBI: Pyrrolidine is a cyclic amine whose five-membered ring contains four carbon atoms and one nitrogen atom; the parent compound of the pyrrolidine family. It is a saturated organic heteromonocyclic parent, a member of pyrrolidines and an azacycloalkane. It is a conjugate base of a pyrrolidinium ion.

Aroma threshold values

Detection: 20.2 ppm

Taste threshold values

Taste characteristics at 50 ppm: ammonia and fishy, amine-like with seaweed and shellfish nuances.

General Description

Pyrrolidine is a saturated heterocycliccompound having one nitrogenatom in a five-membered ring. It is a colorless to pale yellow liquid with an ammonia-like odor. It is found in certain plants andthe ring structure is present in manyalkaloids. Flash point 37°F. Density 0.85 g / cm3. Vapors heavier than air. Produces toxic oxides of nitrogen during combustion.

Air & Water Reactions

Highly flammable. Very soluble in water.

Reactivity Profile

Tetrahydro pyrrole neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides. An explosion occurred when a mixture of Tetrahydro pyrrole, benzaldehyde, and propionic acid was heated in an attempt to form porphyrins.

Hazard

Flammable, dangerous fire risk. Toxic by ingestion and inhalation.

Health Hazard

The acute toxicity of pyrrolidine is moderateon test animals. It is somewhat less toxicthan pyrrole. The vapors are an irritant tothe eyes and respiratory tract. The liquid iscorrosive to the skin. Contact with the eyescan cause damage. The oral LD50 value inrats is 300 mg/kg, while the inhalation LC50value in mice is 1300 mg/m3/2 h (NIOSH1986).

Fire Hazard

Flammable/combustible material. May be ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Flammability and Explosibility

Highlyflammable

Safety Profile

Poison by ingestion and intravenous routes. Moderately toxic by inhalation. Dangerous fire hazard when exposed to heat or flame; can react vigorously with oxidizing materials. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits hghly toxic fumes of NOx.

Purification Methods

Dry pyrrolidine with BaO or sodium, then fractionally distil it, under N2, through a Todd column (p 11) packed with glass helices. [Beilstein 20 H 159, 20 I 36, 20 II 79, 20 III/IV 2072, 20/1 V 162.]

Check Digit Verification of cas no

The CAS Registry Mumber 123-75-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 3 respectively; the second part has 2 digits, 7 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 123-75:
(5*1)+(4*2)+(3*3)+(2*7)+(1*5)=41
41 % 10 = 1
So 123-75-1 is a valid CAS Registry Number.
InChI:InChI=1/C4H9N/c1-2-4-5-3-1/h5H,1-4H2/p+1

123-75-1 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A14852)  Pyrrolidine, 99%   

  • 123-75-1

  • 100ml

  • 223.0CNY

  • Detail
  • Alfa Aesar

  • (A14852)  Pyrrolidine, 99%   

  • 123-75-1

  • 500ml

  • 429.0CNY

  • Detail
  • Alfa Aesar

  • (A14852)  Pyrrolidine, 99%   

  • 123-75-1

  • 2500ml

  • 1523.0CNY

  • Detail
  • Sigma-Aldrich

  • (83240)  Pyrrolidine  puriss. p.a., ≥99.0%

  • 123-75-1

  • 83240-25ML

  • 176.67CNY

  • Detail
  • Sigma-Aldrich

  • (83240)  Pyrrolidine  puriss. p.a., ≥99.0%

  • 123-75-1

  • 83240-100ML

  • 328.77CNY

  • Detail
  • Sigma-Aldrich

  • (83240)  Pyrrolidine  puriss. p.a., ≥99.0%

  • 123-75-1

  • 83240-500ML

  • 907.92CNY

  • Detail
  • Aldrich

  • (394238)  Pyrrolidine  ≥99.5%, purified by redistillation

  • 123-75-1

  • 394238-100ML

  • 672.75CNY

  • Detail
  • Aldrich

  • (394238)  Pyrrolidine  ≥99.5%, purified by redistillation

  • 123-75-1

  • 394238-1L

  • 3,328.65CNY

  • Detail
  • Aldrich

  • (P73803)  Pyrrolidine  99%

  • 123-75-1

  • P73803-5ML

  • 189.54CNY

  • Detail
  • Aldrich

  • (P73803)  Pyrrolidine  99%

  • 123-75-1

  • P73803-100ML

  • 259.74CNY

  • Detail
  • Aldrich

  • (P73803)  Pyrrolidine  99%

  • 123-75-1

  • P73803-500ML

  • 349.83CNY

  • Detail
  • Aldrich

  • (P73803)  Pyrrolidine  99%

  • 123-75-1

  • P73803-2.5L

  • 1,730.43CNY

  • Detail

123-75-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name pyrrolidine

1.2 Other means of identification

Product number -
Other names Tetrahydro pyrrole

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:123-75-1 SDS

123-75-1Synthetic route

pyrrole
109-97-7

pyrrole

pyrrolidine
123-75-1

pyrrolidine

Conditions
ConditionsYield
With 5% Ru/MgO; hydrogen In tetrahydrofuran at 150℃; under 38002.6 Torr; for 0.7h;100%
With dichloro(μ-chloro)(μ-hydrido)bis(η-p-cymene)diruthenium(II); hydrogen In neat (no solvent) at 90℃; under 60006 Torr; for 40h;89%
With Cp*Rh(2-(2-pyridyl)phenyl)H; hydrogen In neat (no solvent) at 100℃; under 27361.8 Torr; for 48h; Catalytic behavior; Glovebox;74%
N-(methoxycarbonyl)pyrrolidine
56475-80-0

N-(methoxycarbonyl)pyrrolidine

pyrrolidine
123-75-1

pyrrolidine

Conditions
ConditionsYield
With tert-butylamine In methanol for 3h; Heating;100%
With methyllithium; lithium bromide In tetrahydrofuran at 0℃; for 1h;95%
1-(pyrrolidinyl)-2,4-dinitronaphthalene
78521-30-9

1-(pyrrolidinyl)-2,4-dinitronaphthalene

methylamine
74-89-5

methylamine

A

pyrrolidine
123-75-1

pyrrolidine

B

1-(Methylamino)-2,4-dinitronaphthalene
39139-78-1

1-(Methylamino)-2,4-dinitronaphthalene

Conditions
ConditionsYield
In water at 30℃; for 1h;A n/a
B 98%
2-pyrrolidinon
616-45-5

2-pyrrolidinon

pyrrolidine
123-75-1

pyrrolidine

Conditions
ConditionsYield
With methanesulfonic acid; ruthenium(1,1,1-tris(di(3,5-dimethylphenyl)phosphinomethyl)ethane)(η4-trimethylenemethane); hydrogen In tetrahydrofuran at 160℃; under 75007.5 Torr; for 16h; Autoclave; Schlenk technique;98%
With tris(pentafluorophenyl)borate; C21H35BrMnNO2P2; potassium tert-butylate; hydrogen In m-xylene at 150℃; under 37503.8 Torr; for 72h;81%
With borane-ammonia complex; boron trifluoride diethyl etherate; tris(pentafluorophenyl)borate In 1,2-dichloro-ethane at 60℃; for 16h;77%
1,4-diaminobutane
110-60-1

1,4-diaminobutane

pyrrolidine
123-75-1

pyrrolidine

Conditions
ConditionsYield
HZSM-5(280) zeolite In water at 300℃; Cyclization;97%
tris(triphenylphosphine)ruthenium(II) chloride In diphenylether at 180℃; for 5h; Product distribution; other α,ω-aliphatic diamines;90%
With carbonylchloro[4,5-bis(diisopropylphosphinomethyl)acridine]hydridoruthenium(II) In 1,4-dioxane; water at 100℃; for 22h; Schlenk technique; Inert atmosphere;88%
pyrrolidine-1-carboxylic acid prop-2-ynyl ester
123477-57-6

pyrrolidine-1-carboxylic acid prop-2-ynyl ester

pyrrolidine
123-75-1

pyrrolidine

Conditions
ConditionsYield
With benzyltriethylammonium tetrathiomolybdate In acetonitrile at 20℃; for 2.5h;97%
Butane-1,4-diol
110-63-4

Butane-1,4-diol

pyrrolidine
123-75-1

pyrrolidine

Conditions
ConditionsYield
With ammonia; hydrogen; CuO/ZnO/Al2O3 at 220℃; under 26252.1 Torr;94%
With aluminum oxide; ammonia at 400℃;
With aluminum oxide; ammonia at 325℃;
ethyl pyrrolidine-1-carboxylate
5470-26-8

ethyl pyrrolidine-1-carboxylate

pyrrolidine
123-75-1

pyrrolidine

Conditions
ConditionsYield
With methyllithium; lithium bromide In tetrahydrofuran at 0℃; for 1h;94%
1-(9-fluorenylmethoxycarbonyl)pyrrolidine
142653-70-1

1-(9-fluorenylmethoxycarbonyl)pyrrolidine

pyrrolidine
123-75-1

pyrrolidine

Conditions
ConditionsYield
With triethylamine; 1-butyl-3-methylimidazolium Tetrafluoroborate In neat (no solvent) at 25℃; for 0.0666667h; Green chemistry;93%
N-benzylpyrrolidine
29897-82-3

N-benzylpyrrolidine

pyrrolidine
123-75-1

pyrrolidine

Conditions
ConditionsYield
With 9,10-Dicyanoanthracene In water; acetonitrile Irradiation;90%
4-Aminobutanol
13325-10-5

4-Aminobutanol

pyrrolidine
123-75-1

pyrrolidine

Conditions
ConditionsYield
With carbonylchloro[4,5-bis(diisopropylphosphinomethyl)acridine]hydridoruthenium(II) In 1,4-dioxane; water at 100℃; for 10h; Schlenk technique; Inert atmosphere;88%
With aluminum oxide; nitrogen at 400℃;
dihydridotetrakis(triphenylphosphine)ruthenium In neat (no solvent) at 155℃; for 24h;79 % Chromat.
C13H14BrN3O3

C13H14BrN3O3

A

pyrrolidine
123-75-1

pyrrolidine

B

5-Bromo-7-nitroindoline
80166-90-1

5-Bromo-7-nitroindoline

Conditions
ConditionsYield
With water In 1,4-dioxane; dichloromethane at 20℃; for 12h; UV-irradiation;A 88%
B n/a
tert-butyl pyrrolidine-1-carboxylate
86953-79-9

tert-butyl pyrrolidine-1-carboxylate

A

pyrrolidine
123-75-1

pyrrolidine

B

isobutene
115-11-7

isobutene

Conditions
ConditionsYield
With methanesulfonic acid In tetrahydrofuran at 45℃; Solvent; Temperature;A 83%
B n/a
With cyclohexene at 260.9℃; under 44 Torr; Kinetics; Further Variations:; Pressures; Temperatures;
N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

pyrrolidine
123-75-1

pyrrolidine

Conditions
ConditionsYield
With isocyanate de chlorosulfonyle In diethyl ether for 10h; Ambient temperature;78%
methanol
67-56-1

methanol

N-(4-methylphenylsulfinyl)pyrrolidine
57671-12-2

N-(4-methylphenylsulfinyl)pyrrolidine

A

pyrrolidine
123-75-1

pyrrolidine

B

methyl p-toluene sulfinate
672-78-6

methyl p-toluene sulfinate

Conditions
ConditionsYield
With tetraethylammonium tosylate Electrochemical reaction; reticulated vitreous carbon anode; Pt cathode;A n/a
B 75%
C20H22NO2S(1+)*BF4(1-)

C20H22NO2S(1+)*BF4(1-)

A

pyrrolidine
123-75-1

pyrrolidine

B

[(methylthio)methyl]-benzene
766-92-7

[(methylthio)methyl]-benzene

C

N1,N2-dimethylphthalamide
19532-98-0

N1,N2-dimethylphthalamide

Conditions
ConditionsYield
With methylamine at 30℃; for 20h;A n/a
B 74%
C n/a
Butane-1,4-diol
110-63-4

Butane-1,4-diol

A

pyrrolidine
123-75-1

pyrrolidine

B

1-butylpyrrolidine
767-10-2

1-butylpyrrolidine

C

4-(pyrrolidin-1-yl)butan-1-ol
93264-47-2

4-(pyrrolidin-1-yl)butan-1-ol

D

1,4-di-(1-pyrrolidinyl)butane
41726-75-4

1,4-di-(1-pyrrolidinyl)butane

E

N-butylamine
109-73-9

N-butylamine

Conditions
ConditionsYield
With ammonia; hydrogen; iron RFC at 260℃; Product distribution; Mechanism; other temp. (280, 300, 310 deg C);A 71%
B 12%
C n/a
D n/a
E 9%
C17H22NO2S(1+)*BF4(1-)

C17H22NO2S(1+)*BF4(1-)

A

pyrrolidine
123-75-1

pyrrolidine

B

sulfure de pentamethylene
1613-51-0

sulfure de pentamethylene

C

N1,N2-dimethylphthalamide
19532-98-0

N1,N2-dimethylphthalamide

Conditions
ConditionsYield
With methylamine at 30℃; for 20h;A n/a
B 71%
C n/a
C20H30NO2S(1+)*BF4(1-)

C20H30NO2S(1+)*BF4(1-)

A

pyrrolidine
123-75-1

pyrrolidine

B

Dibutyl sulfide
544-40-1

Dibutyl sulfide

C

N1,N2-dimethylphthalamide
19532-98-0

N1,N2-dimethylphthalamide

Conditions
ConditionsYield
With methylamine at 30℃; for 20h;A n/a
B 70%
C n/a
C6H12NO(1+)*CH3O4S(1-)
73722-93-7

C6H12NO(1+)*CH3O4S(1-)

A

pyrrolidine
123-75-1

pyrrolidine

B

1-pyrrolidinecarboxaldehyde
3760-54-1

1-pyrrolidinecarboxaldehyde

C

N-nitrosopyrrolidine
930-55-2

N-nitrosopyrrolidine

Conditions
ConditionsYield
With sodium nitrite In waterA n/a
B 70%
C n/a
pyrrolidine
123-75-1

pyrrolidine

succinic acid anhydride
108-30-5

succinic acid anhydride

4-oxo-4-(1-pyrrolidinyl)butanoic acid
69338-35-8

4-oxo-4-(1-pyrrolidinyl)butanoic acid

Conditions
ConditionsYield
In acetonitrile at 20℃;100%
In chloroform for 1h; Heating;83%
With diethyl ether
Reflux;
In toluene for 2.5h; Reflux;
pyrrolidine
123-75-1

pyrrolidine

Nonanoyl chloride
764-85-2

Nonanoyl chloride

1-(pyrrolidin-1-yl)nonan-1-one
20308-70-7

1-(pyrrolidin-1-yl)nonan-1-one

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 14h; Inert atmosphere;100%
With diethyl ether; triethylamine
pyrrolidine
123-75-1

pyrrolidine

undec-10-enoyl chloride
38460-95-6

undec-10-enoyl chloride

1-(pyrrolidin-1-yl)undec-10-en-1-one
95018-99-8

1-(pyrrolidin-1-yl)undec-10-en-1-one

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 14h; Inert atmosphere;100%
With triethylamine In dichloromethane at 0 - 23℃; for 14h;100%
With triethylamine In dichloromethane at 0 - 23℃; for 14h;100%
pyrrolidine
123-75-1

pyrrolidine

Cholest-4-en-3-one
601-57-0

Cholest-4-en-3-one

1-cholesta-3,5-dien-3-yl-pyrrolidine
2309-31-1

1-cholesta-3,5-dien-3-yl-pyrrolidine

Conditions
ConditionsYield
In benzene for 24h; Heating;100%
In benzene100%
93%
pyrrolidine
123-75-1

pyrrolidine

cyclohexane-1,2-epoxide
286-20-4

cyclohexane-1,2-epoxide

(+/-)-trans-[2-(pyrrolidinyl)]cyclohexanol
69420-67-3

(+/-)-trans-[2-(pyrrolidinyl)]cyclohexanol

Conditions
ConditionsYield
for 114h; Heating;100%
With lithium bromide at 20℃; for 2h;100%
With zinc(II) perchlorate hexahydrate at 80℃; for 1h;100%
pyrrolidine
123-75-1

pyrrolidine

cyclohexanone
108-94-1

cyclohexanone

1-(1-Cyclohexen-1-yl)pyrrolidine
1125-99-1

1-(1-Cyclohexen-1-yl)pyrrolidine

Conditions
ConditionsYield
In toluene for 18h; Molecular sieve; Dean-Stark trap; Heating / reflux;100%
With sulfuric acid In toluene Dean-Stark; Reflux;99%
With K-10 Montmorillonite clay In toluene for 2.5h; Heating;95%
pyrrolidine
123-75-1

pyrrolidine

4-chlorobenzonitrile
100-00-5

4-chlorobenzonitrile

1-(4-nitro-phenyl)-pyrrolidine
10220-22-1

1-(4-nitro-phenyl)-pyrrolidine

Conditions
ConditionsYield
In tetrahydrofuran at 50℃; under 4500360 Torr; for 20h;100%
In tetrahydrofuran at 50℃; under 6000 Torr; for 2h; Product distribution; other pressure;100%
at 108℃; for 2h; Neat (no solvent);98%
pyrrolidine
123-75-1

pyrrolidine

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

methyl 3-(pyrrolidin-1-yl)propanoate
22041-21-0

methyl 3-(pyrrolidin-1-yl)propanoate

Conditions
ConditionsYield
With zirconium(IV) chloride In dichloromethane at 20℃; for 0.75h; Michael addition;100%
With silica-supported aluminum chloride at 60℃; for 2h; Michael addition; Neat (no solvent);100%
In dichloromethane at 0 - 20℃; for 2h;100%
pyrrolidine
123-75-1

pyrrolidine

chloroacetyl chloride
79-04-9

chloroacetyl chloride

chloroacetic acid pyrrolidide
20266-00-6

chloroacetic acid pyrrolidide

Conditions
ConditionsYield
In acetone at 20℃;100%
In tetrahydrofuran at 0 - 20℃; for 3.5h;99%
In tetrahydrofuran at 20℃; for 12h; Acylation;98%
pyrrolidine
123-75-1

pyrrolidine

phenylacetyl chloride
103-80-0

phenylacetyl chloride

phenylacetylpyrrolidine
3389-53-5

phenylacetylpyrrolidine

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;100%
With triethylamine In dichloromethane at 20℃; for 14h; Inert atmosphere;100%
With triethylamine In dichloromethane at 20℃;92%
pyrrolidine
123-75-1

pyrrolidine

1-nitropyrrolidine
3760-55-2

1-nitropyrrolidine

Conditions
ConditionsYield
With 2-(trifluoromethyl)-2-propyl nitrate at 50℃; for 168h;100%
With nitronium trifluoromethanesulfonate In dichloromethane at -20℃; for 1h;43%
With tetrachloromethane; dinitrogen pentoxide
With butyl nitrate; ethylmagnesium bromide 1.) benzene, 15 min, 2.) benzene, 0.5 h; Yield given. Multistep reaction;
pyrrolidine
123-75-1

pyrrolidine

Cyclopentene oxide
285-67-6

Cyclopentene oxide

(+/-)-trans-(1-pyrrolidinyl)cyclopentan-2-ol
32635-39-5

(+/-)-trans-(1-pyrrolidinyl)cyclopentan-2-ol

Conditions
ConditionsYield
bismuth(lll) trifluoromethanesulfonate at 160℃; for 0.25h; microwave irradiation;100%
With triethylaluminum 1.) toluene, CH2Cl2, 25-30 deg C, 30 min, 2.) room temperature; Yield given. Multistep reaction;
In water
With potassium carbonate
In ethanol at 80℃; for 18h; Inert atmosphere;
pyrrolidine
123-75-1

pyrrolidine

4-butanolide
96-48-0

4-butanolide

4-hydroxy-1-(pyrrolidin-1-yl)butan-1-one
73200-24-5

4-hydroxy-1-(pyrrolidin-1-yl)butan-1-one

Conditions
ConditionsYield
With triethylamine Inert atmosphere; Reflux;100%
With triethylamine for 16h; Reflux;94%
In benzene for 3h; Heating;90%
pyrrolidine
123-75-1

pyrrolidine

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

5-hydroxy-1-(pyrrolidin-1-yl)pentan-1-one
73200-35-8

5-hydroxy-1-(pyrrolidin-1-yl)pentan-1-one

Conditions
ConditionsYield
With triethylamine Inert atmosphere; Reflux;100%
In benzene82%
pyrrolidine
123-75-1

pyrrolidine

phenylacetic acid
103-82-2

phenylacetic acid

phenylacetylpyrrolidine
3389-53-5

phenylacetylpyrrolidine

Conditions
ConditionsYield
Stage #1: phenylacetic acid With 4-iodofuran-3-yl-boronic acid In dichloromethane for 0.166667h; Molecular sieve 4Å;
Stage #2: pyrrolidine In dichloromethane at 25℃; for 6h; Product distribution / selectivity;
100%
With 4 A molecular sieve at 150℃; for 2h;98%
With tetramethylorthosilicate In toluene at 110℃; for 1h; Inert atmosphere;98%
pyrrolidine
123-75-1

pyrrolidine

p-nitrobenzene iodide
636-98-6

p-nitrobenzene iodide

1-(4-nitro-phenyl)-pyrrolidine
10220-22-1

1-(4-nitro-phenyl)-pyrrolidine

Conditions
ConditionsYield
In tetrahydrofuran at 50℃; under 9000720 Torr; for 20h;100%
With copper(l) iodide; 1-(5,6,7,8-tetrahydroquinolin-8-yl)ethan-1-one; caesium carbonate In N,N-dimethyl-formamide at 25℃; for 24h; Ullmann condensation; Inert atmosphere;95%
With copper(l) iodide In N,N-dimethyl acetamide at 130℃; for 24h;95%
pyrrolidine
123-75-1

pyrrolidine

1-Chlor-4-phenyl-pyridazino<4,5-d>pyridazin
72553-83-4

1-Chlor-4-phenyl-pyridazino<4,5-d>pyridazin

1-Pyrrolidino-4-phenyl-pyridazino<4,5-d>pyridazin
83490-50-0

1-Pyrrolidino-4-phenyl-pyridazino<4,5-d>pyridazin

Conditions
ConditionsYield
for 3h; Heating;100%
pyrrolidine
123-75-1

pyrrolidine

6'-chloro-1,3,1',3'-tetramethyl-3H,1'H-[4,5']bipyrimidinyl-2,6,2',4'-tetraone
74151-83-0

6'-chloro-1,3,1',3'-tetramethyl-3H,1'H-[4,5']bipyrimidinyl-2,6,2',4'-tetraone

1,3,1',3'-Tetramethyl-6-pyrrolidin-1-yl-1H,1'H-[5,5']bipyrimidinyl-2,4,2',4'-tetraone

1,3,1',3'-Tetramethyl-6-pyrrolidin-1-yl-1H,1'H-[5,5']bipyrimidinyl-2,4,2',4'-tetraone

Conditions
ConditionsYield
100%
pyrrolidine
123-75-1

pyrrolidine

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

2-Methylbutyraldehyde
96-17-3, 57456-98-1

2-Methylbutyraldehyde

2,2-Dimethyl-5-(2-methyl-1-pyrrolidin-1-yl-butyl)-[1,3]dioxane-4,6-dione

2,2-Dimethyl-5-(2-methyl-1-pyrrolidin-1-yl-butyl)-[1,3]dioxane-4,6-dione

Conditions
ConditionsYield
In diethyl ether for 0.166667h;100%
pyrrolidine
123-75-1

pyrrolidine

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

d,l-2-ethylhexanal
123-05-7

d,l-2-ethylhexanal

5-(2-Ethyl-1-pyrrolidin-1-yl-hexyl)-2,2-dimethyl-[1,3]dioxane-4,6-dione
93498-12-5

5-(2-Ethyl-1-pyrrolidin-1-yl-hexyl)-2,2-dimethyl-[1,3]dioxane-4,6-dione

Conditions
ConditionsYield
In diethyl ether for 0.166667h;100%
pyrrolidine
123-75-1

pyrrolidine

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

benzaldehyde
100-52-7

benzaldehyde

2,2-Dimethyl-5-(phenyl-pyrrolidin-1-yl-methyl)-[1,3]dioxane-4,6-dione
93498-11-4

2,2-Dimethyl-5-(phenyl-pyrrolidin-1-yl-methyl)-[1,3]dioxane-4,6-dione

Conditions
ConditionsYield
In diethyl ether for 0.166667h;100%
pyrrolidine
123-75-1

pyrrolidine

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

propionaldehyde
123-38-6

propionaldehyde

2,2-Dimethyl-5-(1-pyrrolidin-1-yl-propyl)-[1,3]dioxane-4,6-dione
93498-07-8

2,2-Dimethyl-5-(1-pyrrolidin-1-yl-propyl)-[1,3]dioxane-4,6-dione

Conditions
ConditionsYield
In diethyl ether for 0.166667h;100%
pyrrolidine
123-75-1

pyrrolidine

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

butyraldehyde
123-72-8

butyraldehyde

2,2-Dimethyl-5-(1-pyrrolidin-1-yl-butyl)-[1,3]dioxane-4,6-dione
93498-08-9

2,2-Dimethyl-5-(1-pyrrolidin-1-yl-butyl)-[1,3]dioxane-4,6-dione

Conditions
ConditionsYield
In diethyl ether for 0.166667h;100%
pyrrolidine
123-75-1

pyrrolidine

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

isobutyraldehyde
78-84-2

isobutyraldehyde

2,2-Dimethyl-5-(2-methyl-1-pyrrolidin-1-yl-propyl)-[1,3]dioxane-4,6-dione
93498-09-0

2,2-Dimethyl-5-(2-methyl-1-pyrrolidin-1-yl-propyl)-[1,3]dioxane-4,6-dione

Conditions
ConditionsYield
In diethyl ether for 0.166667h;100%
pyrrolidine
123-75-1

pyrrolidine

formaldehyd
50-00-0

formaldehyd

1-acetyl-3-(2-propynyl)-2-imidazolidone
142238-04-8

1-acetyl-3-(2-propynyl)-2-imidazolidone

1-Acetyl-3-(4-pyrrolidin-1-yl-but-2-ynyl)-imidazolidin-2-one
142237-98-7

1-Acetyl-3-(4-pyrrolidin-1-yl-but-2-ynyl)-imidazolidin-2-one

Conditions
ConditionsYield
With acetic acid; copper(l) chloride In 1,4-dioxane at 50℃; for 4h;100%
pyrrolidine
123-75-1

pyrrolidine

4,5-dihydro-5-phenyl-2(3H)-furanone
1008-76-0

4,5-dihydro-5-phenyl-2(3H)-furanone

4-hydroxy-4-phenyl-1-(pyrrolidine-1-yl)butan-1-one
99802-88-7

4-hydroxy-4-phenyl-1-(pyrrolidine-1-yl)butan-1-one

Conditions
ConditionsYield
With triethylamine Reflux; Inert atmosphere;100%
With triethylamine for 72h; Schlenk technique; Reflux;97%
In water for 4h; Heating;90%
pyrrolidine
123-75-1

pyrrolidine

5,6,9,10,11,11a-Hexahydro-2,3-dimethoxy-8,10-dioxo-8H-benzoquinolizine
5911-65-9

5,6,9,10,11,11a-Hexahydro-2,3-dimethoxy-8,10-dioxo-8H-benzoquinolizine

5,6,11,11a-Tetrahydro-2,3-dimethoxy-8-oxo-10-(1-pyrrolidinyl)-8H-benzoquinolizine
85222-89-5

5,6,11,11a-Tetrahydro-2,3-dimethoxy-8-oxo-10-(1-pyrrolidinyl)-8H-benzoquinolizine

Conditions
ConditionsYield
In benzene for 1h; Heating;100%
pyrrolidine
123-75-1

pyrrolidine

7α,11β-eudesm-4-en-12,6α-olide
18410-00-9

7α,11β-eudesm-4-en-12,6α-olide

(S)-2-((1S,2S,4aR)-1-Hydroxy-4a,8-dimethyl-1,2,3,4,4a,5,6,7-octahydro-naphthalen-2-yl)-1-pyrrolidin-1-yl-propan-1-one

(S)-2-((1S,2S,4aR)-1-Hydroxy-4a,8-dimethyl-1,2,3,4,4a,5,6,7-octahydro-naphthalen-2-yl)-1-pyrrolidin-1-yl-propan-1-one

Conditions
ConditionsYield
In benzene for 30h; Ambient temperature;100%
pyrrolidine
123-75-1

pyrrolidine

(S)-2-((1S,2S,4aR)-1-Hydroxy-4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-2-yl)-1-pyrrolidin-1-yl-propan-1-one

(S)-2-((1S,2S,4aR)-1-Hydroxy-4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-2-yl)-1-pyrrolidin-1-yl-propan-1-one

Conditions
ConditionsYield
In benzene for 18h; Ambient temperature;100%

123-75-1Relevant articles and documents

Photo-oxidation of L-Tyrosine, an Efficient 1,4-Chirality Transfer Reaction

Endo, Katsuya,Seya, Kazuhiko,Hikino, Hiroshi

, p. 934 - 935 (1988)

Dye-sensitized oxidation of L-tyrosine with Rose Bengal yielded the optically pure ketolactam (2) stereoselectively in one step.

-

Sakurai

, p. 374 (1936)

-

Mechanistic Investigations of the Catalytic Formation of Lactams from Amines and Water with Liberation of H2

Gellrich, Urs,Khusnutdinova, Julia R.,Leitus, Gregory M.,Milstein, David

, p. 4851 - 4859 (2015)

The mechanism of the unique lactam formation from amines and water with concomitant H2 liberation with no added oxidant, catalyzed by a well-defined acridine-based ruthenium pincer complex was investigated in detail by both experiment and DFT calculations. The results show that a dearomatized form of the initial complex is the active catalyst. Furthermore, reversible imine formation was shown to be part of the catalytic cycle. Water is not only the oxygen atom source but also acts as a cocatalyst for the H2 liberation, enabled by conformational flexibility of the acridine-based pincer ligand. (Figure Presented).

PHOTOSENSITIZED SINGLE ELECTRON TRANSFER INITIATED N-DEBENZYLATION. A CONVENIENT AND MILD APPROACH

Pandey, G.,Rani, K. Sudha

, p. 4157 - 4158 (1988)

A mild method of N-debenzylation via photosensitized single electron transfer (SET) using 9,10-dicyano anthracene (DCA) as electron acceptor in neutral medium is reported.

N-trifluoroacetylamino alcohols as phosphodiester protecting groups in the synthesis of oligodeoxyribonucleotides

Wilk, Andrzej,Srinivasachar, Kasturi,Beaucage, Serge L.

, p. 6712 - 6713 (1997)

-

-

Brown,van Gulick

, p. 1046 (1956)

-

A Lewis Base Nucleofugality Parameter, NFB, and Its Application in an Analysis of MIDA-Boronate Hydrolysis Kinetics

García-Domínguez, Andrés,Gonzalez, Jorge A.,Leach, Andrew G.,Lloyd-Jones, Guy C.,Nichol, Gary S.,Taylor, Nicholas P.

supporting information, (2022/01/04)

The kinetics of quinuclidine displacement of BH3 from a wide range of Lewis base borane adducts have been measured. Parameterization of these rates has enabled the development of a nucleofugality scale (NFB), shown to quantify and predict the leaving group ability of a range of other Lewis bases. Additivity observed across a number of series R′3-nRnX (X = P, N; R′ = aryl, alkyl) has allowed the formulation of related substituent parameters (nfPB, nfAB), providing a means of calculating NFB values for a range of Lewis bases that extends far beyond those experimentally derived. The utility of the nucleofugality parameter is explored by the correlation of the substituent parameter nfPB with the hydrolyses rates of a series of alkyl and aryl MIDA boronates under neutral conditions. This has allowed the identification of MIDA boronates with heteroatoms proximal to the reacting center, showing unusual kinetic lability or stability to hydrolysis.

Method for protecting sulfonyl of deamination amine

-

Paragraph 0054-0056, (2021/11/03)

The invention discloses a method for removing sulfenyl protection of amine. The method comprises the following steps: dissolving N - sulfonyl-protected amine and a base in a reaction solvent, then adding diphenylphosphine to uniformly mix and maintain 90 °C. When TCL detection reaction is complete, a recrystallization method or an extraction separation method is adopted to obtain the target product. The method disclosed by the invention adopts diphenylphosphine as an extraction reagent, is good in reaction activity, high in selectivity and wide in application range, and can replace the use of a hazardous reagent under the basic heating condition. Prodrug research and development and industrial production are of great significance.

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