30727-14-1

Usage

Uses

Used in Pharmaceutical Industry:
1-Ethyl-3-pyrrolidinol is used as an intermediate in the production of pharmaceuticals for its ability to facilitate the synthesis of various medicinal compounds.
Used in Pesticide Industry:
In the pesticide industry, 1-Ethyl-3-pyrrolidinol is utilized as an intermediate, contributing to the development of effective pest control agents.
Used as a Solvent:
1-Ethyl-3-pyrrolidinol is used as a solvent for resins, dyes, and oils, due to its capacity to dissolve these substances effectively.
Safety Considerations:
While 1-Ethyl-3-pyrrolidinol has low toxicity, it is crucial to handle this chemical with care to avoid respiratory irritation and central nervous system effects that can occur with high-level exposure. Appropriate protective equipment and adherence to safety guidelines are essential when working with 1-ETHYL-3-PYRROLIDINOL.

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 
• 94-71-3 2-Ethoxyphenol 
• 75390-11-3 1-ethyl-3,4-epoxypyrrolidine 
• 2419-74-1 1,4-dichlorobutan-2-ol 

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 
• 902767-83-3 1-((1-ethylpyrrolidin-3-yl)oxy)-4-((5,6-dichloronaphthyloxy)methyl)benzene 
• 1246532-41-1 1-ethyl-3-(3-methyl-4-nitro-phenoxy)-pyrrolidine 
• 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 
• 1061749-49-2 C₂₃H₂₈N₆O₂ 

Relevant academic research and scientific papers

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.

Cis and trans-3-aryloxy-4-hydroxypyrrolidines used as anti-arrhythmics

Cis and trans-3-aryloxy-4-hydroxypyrrolidines and derivatives thereof having the formula: STR1 are disclosed wherein R1 is hydrogen, loweralkyl, benzyloxycarbonyl and N-loweralkylcarbamoyl; R2 is hydrogen, lower alkyl, cycloalkyl, phenylalkyl, benzyloxycarbonyl, carbamoyl, N-loweralkylcarbamoyl, N-diloweralkylcarbamoyl and parafluorobenzoyl-lower-alkyl; Ar is phenyl, substituted phenyl, 1-naphthyl, 2-naphthyl, 1-indenyl and 2-indenyl and pharmaceutically acceptable acid addition and quaternary salts thereof. The compounds have antidepressant, antihypertensive and antiarrythmic activity in animals.