1838-39-7

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 4-(ethoxycarbonyl)piperidine-1-acetate is used as a synthetic intermediate for the preparation of quinuclidine derivatives, which are important in the development of various pharmaceutical compounds. These derivatives exhibit a range of biological activities, including antimicrobial, anti-inflammatory, and analgesic properties, making them valuable in the creation of new drugs and therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, Ethyl 4-(ethoxycarbonyl)piperidine-1-acetate is used as a reagent for the synthesis of complex organic molecules. Its unique structure allows for various chemical reactions, such as nucleophilic substitutions, esterification, and amide formation, which can be employed to create a wide array of chemical products.
Used in Research and Development:
Ethyl 4-(ethoxycarbonyl)piperidine-1-acetate is also utilized in research and development settings, where it can be employed to study the synthesis and properties of quinuclidine derivatives and other related compounds. This can lead to a better understanding of their potential applications and the development of new synthetic methods and techniques.

InChI:InChI=1/C12H21NO4/c1-3-16-11(14)9-13-7-5-10(6-8-13)12(15)17-4-2/h10H,3-9H2,1-2H3

Synthetic route

chloroacetic acid ethyl ester (105-39-5) + piperidine-4-carboxylic acid ethyl ester hydrochloride → ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7)

Conditions	Yield
Stage #1: piperidine-4-carboxylic acid ethyl ester hydrochloride With potassium carbonate In acetonitrile at 20℃; for 0.166667h; Stage #2: chloroacetic acid ethyl ester In acetonitrile at 20℃; for 5.5h;	93.1%

4-carbethoxypiperidine (1126-09-6) + chloroacetic acid ethyl ester (105-39-5) → ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7)

Conditions	Yield
With potassium carbonate

isonicotinic acid ethylester (1570-45-2) → ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: Raney nickel; dioxane / 175 - 180 °C / 91938.4 Torr / Hydrogenation 2: K2CO3 View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → 3-Quinuclidinone (3731-38-2)

Conditions	Yield
With potassium; toluene anschliessend mit konz. Salzsaeure;
With potassium ethoxide; toluene anschliessend mit konz. Salzsaeure;

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → 2-ethoxycarbonyl-3-quinuclidinone (34286-16-3)

Conditions	Yield
With potassium ethoxide; toluene
With potassium tert-butylate In toluene for 4.5h; Dieckmann Condensation; Reflux; Inert atmosphere;

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → 3-(3-oxo-quinuclidin-2-yl)-propionitrile (99169-54-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium ethylate; toluene / anschliessend mit konz. Salzsaeure 2: methanol. KOH; tert-butyl alcohol View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → 2,2-bis-(2-cyano-ethyl)-quinuclidin-3-ol (105788-47-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium ethylate; toluene / anschliessend mit konz. Salzsaeure 2: tert-butyl alcohol; acrylonitrile; methanol. KOH 3: LiAlH4; diethyl ether; benzene / 65 - 70 °C View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → 3,3'-(3-oxo-quinuclidine-2,2-diyl)-di-propionitrile (100705-63-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium ethylate; toluene / anschliessend mit konz. Salzsaeure 2: tert-butyl alcohol; acrylonitrile; methanol. KOH View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → 3,3'-(3-oxo-quinuclidine-2,2-diyl)-di-propionic acid

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium ethylate; toluene / anschliessend mit konz. Salzsaeure 2: tert-butyl alcohol; acrylonitrile; methanol. KOH 3: acetic acid; concentrated aqueous HCl View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → Quinuclidine (100-76-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium; toluene / anschliessend mit konz. Salzsaeure 2: hydrazine hydrate; sodium ethylate; ethanol / 175 °C View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → quinuclidinyl benzilate (6581-06-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium; toluene / anschliessend mit konz. Salzsaeure 2: lithium alanate; diethyl ether 3: sodium; toluene / Behandeln mit Chlor-diphenyl-acetylchlorid und Erwaermen des Reaktionsgemisches mit wss. Salzsaeure View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → 2,2-diphenyl-pent-4-enoic acid quinuclidin-3-yl ester

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium; toluene / anschliessend mit konz. Salzsaeure 2: lithium alanate; diethyl ether 3: sodium; toluene / Behandeln mit 2,2-Diphenyl-pent-4-enoylchlorid View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → 3-bromo-quinuclidine; hydrobromide (99310-69-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium; toluene / anschliessend mit konz. Salzsaeure 2: lithium alanate; diethyl ether 3: concentrated aqueous hydrobromic acid / 180 °C View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → fluorene-9-carboxylic acid quinuclidin-3-yl ester

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium; toluene / anschliessend mit konz. Salzsaeure 2: lithium alanate; diethyl ether 3: benzene View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → (S)-quinuclidin-3-ol (3684-26-2, 25333-42-0, 34583-34-1, 1619-34-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium; toluene / anschliessend mit konz. Salzsaeure 2: lithium alanate; diethyl ether 3: (1S)-2-oxo-bornane-10-sulfonic acid View Scheme
Multi-step reaction with 6 steps 1.1: potassium tert-butylate / toluene / 4.5 h / Reflux; Inert atmosphere 2.1: Reflux 2.2: 20 °C 3.1: sodium hydroxide; water / 0.5 h / -5 - 0 °C 3.2: 1.5 h 4.1: 2 h / 20 °C 5.1: ethanol; water / 0.33 h / 50 °C 6.1: sodium hydroxide / water / 1 h / 70 °C View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → (R)-quinuclidin-3-ol (25333-42-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium; toluene / anschliessend mit konz. Salzsaeure 2: lithium alanate; diethyl ether 3: (1S)-2-oxo-bornane-10-sulfonic acid View Scheme
Multi-step reaction with 6 steps 1.1: potassium tert-butylate / toluene / 4.5 h / Reflux; Inert atmosphere 2.1: Reflux 2.2: 20 °C 3.1: sodium hydroxide; water / 0.5 h / -5 - 0 °C 3.2: 1.5 h 4.1: 2 h / 20 °C 5.1: ethanol; water / 0.33 h / 50 °C 6.1: sodium hydroxide / water / 1 h / 70 °C View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → 3-quinuclidinol (1619-34-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium; toluene / anschliessend mit konz. Salzsaeure 2: lithium alanate; diethyl ether View Scheme
Multi-step reaction with 3 steps 1.1: potassium tert-butylate / toluene / 4.5 h / Reflux; Inert atmosphere 2.1: Reflux 2.2: 20 °C 3.1: sodium hydroxide; water / 0.5 h / -5 - 0 °C 3.2: 1.5 h View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → (R)-diphenylacetic acid quinuclidin-3-yl ester (62078-97-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium; toluene / anschliessend mit konz. Salzsaeure 2: lithium alanate; diethyl ether 3: (1S)-2-oxo-bornane-10-sulfonic acid 4: benzene View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → 3-(Diphenylacetyloxy)quinuclidine (62078-97-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium; toluene / anschliessend mit konz. Salzsaeure 2: lithium alanate; diethyl ether 3: benzene View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → 3-quinuclidinone hydrochloride (1193-65-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium tert-butylate / toluene / 4.5 h / Reflux; Inert atmosphere 2.1: Reflux 2.2: 20 °C View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → 3-acetoxyquinuclidine (827-61-2, 59653-40-6, 59653-42-8, 72353-53-8)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: potassium tert-butylate / toluene / 4.5 h / Reflux; Inert atmosphere 2.1: Reflux 2.2: 20 °C 3.1: sodium hydroxide; water / 0.5 h / -5 - 0 °C 3.2: 1.5 h 4.1: 2 h / 20 °C View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → (R)-3-acetoxyquinuclidinium L-tartrate

Conditions	Yield
Multi-step reaction with 5 steps 1.1: potassium tert-butylate / toluene / 4.5 h / Reflux; Inert atmosphere 2.1: Reflux 2.2: 20 °C 3.1: sodium hydroxide; water / 0.5 h / -5 - 0 °C 3.2: 1.5 h 4.1: 2 h / 20 °C 5.1: ethanol; water / 0.33 h / 50 °C View Scheme

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate (1838-39-7) → (S)-3-acetoxyquinuclidinium D-tartrate

Conditions	Yield
Multi-step reaction with 5 steps 1.1: potassium tert-butylate / toluene / 4.5 h / Reflux; Inert atmosphere 2.1: Reflux 2.2: 20 °C 3.1: sodium hydroxide; water / 0.5 h / -5 - 0 °C 3.2: 1.5 h 4.1: 2 h / 20 °C 5.1: ethanol; water / 0.33 h / 50 °C View Scheme

Upstream product

• 1126-09-6 4-carbethoxypiperidine 
• 105-39-5 chloroacetic acid ethyl ester 
• 1570-45-2 isonicotinic acid ethylester 

Downstream Products

• 1193-65-3 3-quinuclidinone hydrochloride 
• 827-61-2 3-acetoxyquinuclidine 
• 62078-97-1 3-(Diphenylacetyloxy)quinuclidine 
• 62078-97-1 (R)-diphenylacetic acid quinuclidin-3-yl ester 
• 1619-34-7 3-quinuclidinol 
• 25333-42-0 (R)-quinuclidin-3-ol 
• 3684-26-2 (S)-quinuclidin-3-ol 
• 6581-06-2 quinuclidinyl benzilate 
• 100-76-5 Quinuclidine 
• 34286-16-3 2-ethoxycarbonyl-3-quinuclidinone 
• 3731-38-2 3-Quinuclidinone 

Relevant academic research and scientific papers

Preparation method of optical activity 3-quinuclidinol

The invention relates to an intermediate synthesis method, belongs to the field of organic synthesis, and particularly relates to a preparation method of optical activity 3-quinuclidinol with the advantages that the operation is simple and convenient, the cost is low, and the method is suitable for industrial production. An intermediate of 3-quinuclidinol is obtained by using 4-nipecotic acid as astarting material through esterification, nucleophilic substitution, Dieckmann condensation, decarboxylation, salification, reduction, acetylization, chemical resolution and the like. The reaction formula is shown in the description.