30727-14-1

Basic information

• Product Name: 1-ETHYL-3-PYRROLIDINOL
• Synonyms: N-Ethyl-3-hydroxypyrrolidine;NSC 88610;1-ethyl-3-hydroxy-terthydropyrrolo;1-ethyl-3-pyrrolidino;3-Pyrrolidinol, 1-ethyl-;1-ETHYL-3-PYRROLIDINOL;1-ETHYL-3-HYDROXYPYRROLIDINE;Ethylpyrrolidinol
• CAS NO: 30727-14-1
• Molecular Formula: C₆H₁₃NO
• Molecular Weight: 115.17
• EINECS: 250-310-7
• Product Categories: Heterocycles;Building Blocks;Heterocyclic Building Blocks;Pyrrolidines
• Mol File: 30727-14-1.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 59-61 °C1 mm Hg(lit.)
• Flash Point: 165 °F
• Appearance: /
• Density: 0.967 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0629mmHg at 25°C
• Refractive Index: n20/D 1.467(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.83±0.20(Predicted)
• CAS DataBase Reference: 1-ETHYL-3-PYRROLIDINOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ETHYL-3-PYRROLIDINOL(30727-14-1)
• EPA Substance Registry System: 1-ETHYL-3-PYRROLIDINOL(30727-14-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• RTECS: UY5685500
• Hazardous Substances Data: 30727-14-1(Hazardous Substances Data)

Usage

General Description

1-Ethyl-3-pyrrolidinol is a chemical compound that is also known as N-ethyl-3-pyrrolidinol. It is a colorless to pale yellow liquid with a faint amine-like odor. This chemical is used as an intermediate in the manufacture of pharmaceuticals, pesticides, and other organic compounds. It is also used as a solvent for resins, dyes, and oils. 1-Ethyl-3-pyrrolidinol has low toxicity, but exposure to high levels can cause respiratory irritation and central nervous system effects. It is important to handle this chemical with caution, following safety guidelines and using appropriate protective equipment.

InChI:InChI=1/C6H13NO/c1-2-7-4-3-6(8)5-7/h6,8H,2-5H2,1H3/t6-/m1/s1

Synthetic route

1,4-dichlorobutan-2-ol (2419-74-1) + ethylamine (75-04-7) → N-ethyl-3-hydroxypyrrolidine (30727-14-1)

Conditions	Yield
In water at 10 - 120℃; under 6750.68 Torr; for 10h; Autoclave; Sealed tube;	66.1%

1,4-dibromo-2-butanol (19398-47-1) + ethylamine (75-04-7) → N-ethyl-3-hydroxypyrrolidine (30727-14-1)

Conditions	Yield
With ethanol at 100 - 130℃;

1-ethyl-pyrrolidin-3-one → N-ethyl-3-hydroxypyrrolidine (30727-14-1)

Conditions	Yield
With sodium borate; water

ethylamine (75-04-7) + (+-)-1,4-dichloro-butan-2-ol → N-ethyl-3-hydroxypyrrolidine (30727-14-1)

Conditions	Yield
With ethanol at 90℃;

2-Ethoxyphenol (94-71-3) + 1-ethyl-3,4-epoxypyrrolidine → N-ethyl-3-hydroxypyrrolidine (30727-14-1)

Conditions	Yield
With hydrogenchloride; sodium hydroxide In dichloromethane

N-ethyl-3-hydroxypyrrolidine (30727-14-1) + p-toluenesulfonyl chloride (98-59-9) → toluene-4-sulfonic acid 1-ethylpyrrolidin-3-yl ester (957621-58-8)

Conditions	Yield
With triethylamine In dichloromethane for 3h;	74.9%

N-ethyl-3-hydroxypyrrolidine (30727-14-1) + (2R)-2-cyclopentyl-2-hydroxy-2-phenylacetic acid (64471-45-0) → (2R)-2-cyclopentyl-2-hydroxy-2-phenylacetic acid 1-ethylpyrrolidin-3-yl ester

Conditions	Yield
Stage #1: (2R)-2-cyclopentyl-2-hydroxy-2-phenylacetic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: N-ethyl-3-hydroxypyrrolidine With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 15h;	65%

N-ethyl-3-hydroxypyrrolidine (30727-14-1) + 4-fluorophenyl 2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl ketone (193966-49-3) → 4-[(1-Ethylpyrrolidin-3-yl)oxy]phenyl 2-[4-[2-(1-Pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl Ketone

Conditions	Yield
In N,N-dimethyl-formamide	63%

N-ethyl-3-hydroxypyrrolidine (30727-14-1) + C36H48N2O2 → C42H59N3O2

Conditions	Yield
Stage #1: C36H48N2O2 With oxalyl dichloride In dichloromethane at 20℃; for 24h; Stage #2: N-ethyl-3-hydroxypyrrolidine With triethylamine In dichloromethane at 20℃; for 8h;	48%

N-ethyl-3-hydroxypyrrolidine (30727-14-1) + 2-amino-4-(2,4-dichloro-5-hydroxyphenyl)thieno[2,3-d]pyrimidine-6-carboxylic acid ethylamide (847559-68-6) → 2-amino-4-[2,4-dichloro-5-(1-ethyl-pyrrolidin-3-yloxy)phenyl]thieno[2,3-d]pyrimidine-6-carboxylic acid ethylamide (908002-40-4)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 16h; Mitsunobu reaction;	41%

N-ethyl-3-hydroxypyrrolidine (30727-14-1) + 2,4-diferrocenyl-1,3-dithiadiphosphetane-2,4-disulfide (182944-97-4, 343251-03-6) → (O-1-ethyl-3-pyrrolidinium)ferrocenyldithiophosphonate (1005195-40-3)

Conditions	Yield
In toluene (FcPS(μ-S))2 treated with 1-ethyl-3-pyrrolidinol in toluene; mixture heated for 30-45 min; obtained solid isolated by filtration and extracted 3 times with hot CHCl3; CHCl3 removed at room temp.; elem. anal.;	39%

N-ethyl-3-hydroxypyrrolidine (30727-14-1) + 2-chloronicotinic acid (2942-59-8) → Sodium; 2-(1-ethyl-pyrrolidin-3-yloxy)-nicotinate

Conditions	Yield
With sodium hydride In dimethyl sulfoxide at 60℃;

N-ethyl-3-hydroxypyrrolidine (30727-14-1) + 3-[4-(2-piperidin-1-yl-ethoxy)-benzyl]-2-(4-triisopropylsilanyloxy-phenyl)-benzo[b]thiophen-6-ol → 2-[4-(1-ethyl-pyrrolidin-3-yloxy)-phenyl]-3-[4-(2-piperidin-1-yl-ethoxy)-benzyl]-benzo[b]thiophen-6-ol

Conditions	Yield
Multistep reaction;

N-ethyl-3-hydroxypyrrolidine (30727-14-1) + 3-HYDROXYPYRIDINE (109-00-2) → 3-(1-Ethyl-3-pyrrolidinyloxy)-pyridine

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran Mitsunobu reaction;

N-ethyl-3-hydroxypyrrolidine (30727-14-1) → 2-[2-(Dimethylamino)ethyl]-4-ethyl-2,3-dihydropyrido[3,2-f][1,4]oxazepin-5(4H)-thione (91836-98-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: NaH / dimethylsulfoxide / 60 °C 2: 1) HCl(g), 2) triphenylphosphine, CCl4 / 1) CHCl3, -> pH 6, 2) reflux 3: P4S10 / CHCl3 / Heating 4: 39 percent / Ambient temperature View Scheme

N-ethyl-3-hydroxypyrrolidine (30727-14-1) → 8-(2-Chloro-ethyl)-6-ethyl-7,8-dihydro-6H-9-oxa-1,6-diaza-benzocyclohepten-5-one (91833-28-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaH / dimethylsulfoxide / 60 °C 2: 1) HCl(g), 2) triphenylphosphine, CCl4 / 1) CHCl3, -> pH 6, 2) reflux View Scheme

N-ethyl-3-hydroxypyrrolidine (30727-14-1) → 8-(2-Chloro-ethyl)-6-ethyl-7,8-dihydro-6H-9-oxa-1,6-diaza-benzocycloheptene-5-thione (91837-18-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: NaH / dimethylsulfoxide / 60 °C 2: 1) HCl(g), 2) triphenylphosphine, CCl4 / 1) CHCl3, -> pH 6, 2) reflux 3: P4S10 / CHCl3 / Heating View Scheme

N-ethyl-3-hydroxypyrrolidine (30727-14-1) + tert-butyl 4-(2-hydroxyphenyl)piperazine-1-carboxylate (313657-51-1) → 4-[2-(1-ethyl-pyrrolidin-3-yloxy)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester (1106056-84-1)

Conditions	Yield
Mitsunobu reaction;

N-ethyl-3-hydroxypyrrolidine (30727-14-1) → 1-ethylpyrrolidin-3-ol sodium salt (616866-20-7)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide

N-ethyl-3-hydroxypyrrolidine (30727-14-1) + N-[2-(3,5-dimethyl-pyrazol-1-yl)-6-(3-hydroxy-phenyl)-pyrimidin-4-yl]-acetamide (1061750-36-4) → C23H28N6O2 (1061749-49-2)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 12h; Mitsunobu reaction;

N-ethyl-3-hydroxypyrrolidine (30727-14-1) + 5-((4-iodophenyl)methoxy)-1,2-dichloronaphthalene (902767-82-2) → 1-((1-ethylpyrrolidin-3-yl)oxy)-4-((5,6-dichloronaphthyloxy)methyl)benzene (902767-83-3)

Conditions	Yield
Stage #1: N-ethyl-3-hydroxypyrrolidine With methyllithium In 1,2-dimethoxyethane; diethyl ether at 0℃; for 0.166667h; Stage #2: With copper(l) chloride In 1,2-dimethoxyethane; diethyl ether at 0 - 20℃; for 0.5h; Stage #3: 5-((4-iodophenyl)methoxy)-1,2-dichloronaphthalene With pyridine In 1,2-dimethoxyethane; diethyl ether at 20℃; for 48h; Heating / reflux;

N-ethyl-3-hydroxypyrrolidine (30727-14-1) + 3-methyl-4-nitrophenol (2581-34-2) → 1-ethyl-3-(3-methyl-4-nitro-phenoxy)-pyrrolidine (1246532-41-1)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Inert atmosphere;

Upstream product

• 19398-47-1 1,4-dibromo-2-butanol 
• 75-04-7 ethylamine 
• 2419-74-1 1,4-dichlorobutan-2-ol 
• 94-71-3 2-Ethoxyphenol 
• 75390-11-3 1-ethyl-3,4-epoxypyrrolidine 

Downstream Products

• 957621-58-8 toluene-4-sulfonic acid 1-ethylpyrrolidin-3-yl ester 
• 1106056-84-1 4-[2-(1-ethyl-pyrrolidin-3-yloxy)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester 
• 1061749-49-2 C₂₃H₂₈N₆O₂ 
• 1246532-41-1 1-ethyl-3-(3-methyl-4-nitro-phenoxy)-pyrrolidine 
• 902767-83-3 1-((1-ethylpyrrolidin-3-yl)oxy)-4-((5,6-dichloronaphthyloxy)methyl)benzene 
• 908002-40-4 2-amino-4-[2,4-dichloro-5-(1-ethyl-pyrrolidin-3-yloxy)phenyl]thieno[2,3-d]pyrimidine-6-carboxylic acid ethylamide 

Relevant articles and documents

Preparation method of N-substituent-3-hydroxytetrahydropyrrole

The invention discloses a preparation method of N-substituent-3-hydroxytetrahydropyrrole. The preparation method takes 1,2,4-butanetriol as a starting material, and comprises the following steps: performing a halogenating reaction between the starting material and hydrogen halide to prepare an intermediate 1,4-dihalogeno-2-butanol first, and then performing a condensation reaction with primary amine RNH2 to obtain a target product, wherein R represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tertiary butyl or benzyl; the halogenating reaction is performed in the presence of an acidic catalyst, and the acidic catalyst is formic acid or acetic acid; and hydrogen halide is hydrogen chloride or hydrogen bromide. The preparation method disclosed by the invention is relatively short in synthetic route, the starting material 1,2,4-butanetriol is low in price and easy to obtain, and other materials used in the method are relatively high in safety and also relatively low in price, so that the preparation method is suitable for industrial large-scale production. Particularly, the halogenating reaction can obtain a yield of 50% or above by selection of suitable halogenating agents and catalysts.