1-Azabicyclo[2.2.2]octane-4-carboxylic acid ethyl ester
- Product Name
- 1-Azabicyclo[2.2.2]octane-4-carboxylic acid ethyl ester
- CAS No.
- 22766-68-3
- Chemical Name
- 1-Azabicyclo[2.2.2]octane-4-carboxylic acid ethyl ester
- Synonyms
- UMECLIDINIUM INT;Quinuclidine-4-carboxylic acid ethyl ester;ethyl-1-azabicyclo[2.2.2]octane-4-carboxylate;azabicyclo[2.2.2]octane-4-carboxylic acid ethyl ester;1-Azabicyclo[2.2.2]octane-4-carboxylic acid ethyl ester;Diphenyl(quinuclidin-4-yl)methanolEthyl quinuclidine-4-carboxylate
- CBNumber
- CB62240411
- Molecular Formula
- C10H17NO2
- Formula Weight
- 183.25
- MOL File
- 22766-68-3.mol
1-Azabicyclo[2.2.2]octane-4-carboxylic acid ethyl ester Property
- Boiling point:
- 233.4±40.0 °C(Predicted)
- Density
- 1.09±0.1 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Room Temperature
- pka
- 9.44±0.12(Predicted)
- Appearance
- Colorless to light yellow Liquid
- InChI
- InChI=1S/C10H17NO2/c1-2-13-9(12)10-3-6-11(7-4-10)8-5-10/h2-8H2,1H3
- InChIKey
- MMXIVBVOFFBDEB-UHFFFAOYSA-N
- SMILES
- N12CCC(C(OCC)=O)(CC1)CC2
Safety
- HS Code
- 2933998090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
- Precautionary statements
-
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P332+P313IF SKIN irritation occurs: Get medical advice/attention.
P337+P313IF eye irritation persists: Get medical advice/attention.
N-Bromosuccinimide Price
- Product number
- E925945
- Product name
- Ethyl4-Quinuclidinecarboxylate
- Packaging
- 1g
- Price
- $95
- Updated
- 2021/12/16
- Product number
- CS-M1578
- Product name
- Ethylquinuclidine-4-carboxylate
- Purity
- 99.25%
- Packaging
- 1g
- Price
- $70
- Updated
- 2021/12/16
- Product number
- 3657AH
- Product name
- Ethylquinuclidine-4-carboxylate
- Packaging
- 1g
- Price
- $140
- Updated
- 2021/12/16
- Product number
- CS-M1578
- Product name
- Ethylquinuclidine-4-carboxylate
- Purity
- 99.25%
- Packaging
- 5g
- Price
- $205
- Updated
- 2021/12/16
- Product number
- 4H58-1-541
- Product name
- Ethyl quinuclidine-4-carboxylate
- Packaging
- 250mg
- Price
- $247
- Updated
- 2021/12/16
1-Azabicyclo[2.2.2]octane-4-carboxylic acid ethyl ester Chemical Properties,Usage,Production
Uses
Ethyl 4-Quinuclidinecarboxylate is a reactant used in the synthesis of azoniabicyclooctanes as muscarinic acetylcholine receptor antagonists.
Synthesis
869112-14-1
22766-68-3
General procedure: ethyl 1-(2-chloroethyl)piperidine-4-carboxylate (II) (5.0 g, 22.76 mmol) was dissolved in tetrahydrofuran (THF, 147.0 mL) under nitrogen protection and the solution was cooled to -50 °C. At -50 °C, LDA (2.0 M in heptane/THF/ethylbenzene, 17.0 mL, 34.0 mmol) was added slowly over 25 min. The reaction mixture was gradually warmed to room temperature over 16 hours. Upon completion of the reaction, the reaction was quenched with saturated aqueous K2CO3 solution (122.0 mL) and extracted with ether (3 x 120.0 mL). The organic layers were combined, dried with MgSO4, filtered and concentrated under reduced pressure. The resulting orange liquid was co-evaporated three times with dichloromethane to remove excess ethylbenzene, resulting in an orange oily product (4.15 g, 99.4% yield). The product was ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (III) with the following 1H-NMR (300 MHz, CDCl3) data: δ4.10 (t, J=5.23 Hz, 2H), 2.90-2.85 (m, 6H), 1.71-1.66 (m, 6H), 1.22 (t, J=4.0 Hz, 3H).
References
[1] Patent: WO2018/87561, 2018, A1. Location in patent: Page/Page column 13
[2] Patent: US2007/185155, 2007, A1. Location in patent: Page/Page column 9
[3] Journal of Medicinal Chemistry, 2009, vol. 52, # 8, p. 2493 - 2505
[4] Patent: WO2005/112644, 2005, A2. Location in patent: Page/Page column 13
[5] Angewandte Chemie - International Edition, 2017, vol. 56, # 4, p. 1152 - 1157
1-Azabicyclo[2.2.2]octane-4-carboxylic acid ethyl ester Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 1-Azabicyclo[2.2.2]octane-4-carboxylic acid ethyl ester manufacturers
- Product
- Ethyl quinuclidine-4-carboxylate 22766-68-3
- Price
- US $2.00-6.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 100kg
- Release date
- 2025-08-05
- Product
- 1-Azabicyclo[2.2.2]octane-4-carboxylic acid ethyl ester 22766-68-3
- Price
- US $7.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 100kg
- Release date
- 2020-02-13